gypsy wind sailboat

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Alaska Sailing Yachts

S/v gypsy wind.

Tongass National Forest, Sitka, Juneau, Petersburg, Inside Passage

May-September

Days/Nights

Charter rate.

There is no place more spectacular in Alaska then the Inside Passage, one of the two remaining temperate rainforests left in this world. While sailing these enchanting waters you will experience the best of Alaska. Whether you are interested in whale watching, observing bears, birding, fishing, glacier viewing, hiking or kayaking, there is no better place than the Inside Passage. GYPSY WIND offers custom trips based on your interests. If your pleasure is photographing bears feeding, seeing breaching whales, kayaking through icebergs, hooking a big fish, or a mix of visiting small towns and exploring the wild the crew can accommodate your every need and look forward to sharing this adventure with you.

Join the crew of Sailing Yacht Gypsy Wind. The sailboat is completely equipped for your safety and comfort. Gypsy Wind is a Irwin 72’ sailboat equipped with 1 queen and 2 double staterooms with in-suite bathrooms, a large comfortable main salon, and a spacious cockpit and a jacuzzi to relax and see all the breathtaking sights Alaska has to offer. The crew includes a USCG Captain, with a 500 Ton Master Captains license, and a professional culinary trained chef who can cook to your heart’s desires.

Sailing Yacht Gypsy Wind operates in the breathtaking waters of southeast Alaska, departing out of their home port of Juneau. The city is served daily by Alaska Airlines jet services.

Most of their sailing area in Alaska is the 20 million acres of the Tonga’s National Forest and small towns in southeast Alaska. In this remote area you’ll spend most evenings anchored in quiet inlets. The Inside Passage is protected from swells from the oceans outer coast and is filled with jaw-dropping bays, beaches, mountains and forest.

The crew on sailing yacht Gypsy Wind love sailing and will put up the sails whenever the wind will allow. They look forward to having people with all levels of sailing experience on their boat and are happy to have guests help sail Gypsy Wind or just sit back and take in the sights. No sailing experience is necessary to join in the adventure.

Sailing yacht Gypsy Wind’s schedule will be custom-designed to your interests in Alaska to maximize your experience. There are many itineraries along each route as well as hundreds of different anchorages along the way. You could sail in Alaska for years and never anchor in the same place twice.

Captain and Crew

Captain: Jonathan Yoors  – Jonathan is originally from Rockport Massachusetts, a small fishing village an hour north of Boston. He has captained boats all over the world but his favorite place to sail and spend time is in the Caribbean and Alaska. Jonathan is a USCG 500ton captain with over 11 years yachting experience and 15 years owning and captaining his own boats, you can rest assured knowing you have an experienced captain at the helm. Jonathan loves to fish, spear fish, snorkel, hike, kayak, paddle board, explore the wilderness and enjoy all types of nature and wildlife the Caribbean and Alaska has to offer.

Chef / Mate: Brittany Battistoni – Brittany is originally a southern California native with a love of traveling the world. She is a professionally trained chef with nearly 15 years professional food service experience. She is also an avid naturalist and enjoys opening the minds of those around her by taking them foraging for local wild edibles in the areas she is on charter in. Brittany is very passionate about food, the environment, critter watching, kayaking, paddle boarding, spear fishing, snorkeling, and other water sports. You can expect to enjoy exceptional locally caught food while chartering GYPSY WIND.

Jonathan and Brittany are a married couple who have been exploring the world together for 6 years now. They have sailed around the east coast of the US and the Caribbean for 3 years, cruised Alaska for 2 years, and sailed across the Atlantic. They both share a love of adventure and a deep love for nature.

Vessel Specifications

• Length: 72 feet
• Beam: 18 feet
• Draft: 7 feet
• Number of Cabins: 5 total; 3 guest cabins each with ensuite head
• Builder/Designer: Ted Irwin
• Refit: 2018
• Number of Crew: 2

Tenders & Toys

• 14 foot custom tender with 25 hp outboard
• 3 tandem kayaks
• Fishing gear
• On deck jacuzzi
• Fully enclosed cockpit
• 2 full heating systems
• All meals and non-alcoholic beverages
• Guided activities
• Fuel and yacht operating costs
• Professional crew

Not Included

• Transportation to/from Alaska and the yacht
• Fishing license
• The chance to see active calving glaciers
• The amazing Alaskan wildlife!
• Experience a private cruise that caters to your every want and desires!

Specifications

• Trip Inquiry

Available Add-ons

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Gypsy Wind, Alaska

Flexible booking.

Set sail aboard the Gypsy Wind sailing yacht for a fantastic adventure cruise in Alaska. Customized to high specifications, the SV Gypsy Wind Alaska offers everything on board for a unique vacation of a lifetime. The interior accommodations, which are comparable to much larger yachts, include a comfortable main salon, spacious walk-in cockpit and 3 guest staterooms. Each stateroom features private en-suite bathrooms, full-sized beds and ample storage space. There is also a reading light and fan for added comfort. The master stateroom also boasts a king-sized bed, small couch, desk and even a bathtub in the en-suite.

Dine under the stars on delicious local cuisine, freshly prepared by the onboard culinary trained chef. Guests will have the opportunity to hunt and forage for wild edibles such as berries, herbs, vegetables, mushrooms, and much more, as the Gypsy Wind delivers both outdoor and culinary adventures. End a day of adventuring unwinding in the spacious jacuzzi located on the aft deck.

Nature-lovers will love their time aboard the Gypsy Wind sailboat, and the passionate and experienced crew are looking forward to sharing the beauty of Alaska with everyone. Cruises range from 7-14-nights and explore South-East Alaska's stunning breathtaking scenery. Hiking, kayaking and fishing are on the agenda. From whale watching to glaciers, sea-lions to bears, a small-ship sailing cruise aboard the Gypsy Wind will make memories to last a lifetime.

Cruises in Alaska sell fast, so call us or book online today to reserve your space.

Choose your departure date adventure cruise | no scuba diving

Included: VAT, Fuel Surcharge, National Park Fees, Port Fees, Drinking Water, Soft drinks, Tea & Coffee, Beach BBQ, Full-Board Meal Plan (All meals), Snacks, Special Dinner, Kayaks, Land Excursions, Naturalist Guide, Beach Towels, Cabin Towels, Deck Towels.

Optional Extras: Gratuities, Airport Transfer, Hotel Transfer, Alcoholic Beverages, Complimentary Toiletries, Laundry / Pressing Services, WiFi internet.

Book now, pay later: You can easily place your booking online. We will then hold the spaces for you and you can confirm with a payment later.

* Extra fees are shown per person.

Pay by bank transfer or online with Best Price Guaranteed

Boat features

• Audio & video entertainment
• Air Conditioned saloon
• Aircon Cabins
• Indoor Saloon
• Warm Water Showers
• Outdoor Dining
• Charging stations
• En-Suite bathrooms
• Non-Smoking Rooms
• Outside Showers
• Family Cabins
• Kayaks On-Board
• Dedicated Local & International Crew
• Nearly 1:1 Crew-to-Guest Ratio
• Leisure Deck
• Observation Deck
• Budget Friendly Cruise
• Family Friendly Cruise
• Available for Charter
• Jacuzzi / Hot Tub

Food & Drinks

• Western Food
• Vegetarian Options
• Snacks All Day
• Vegan Options
• Free Soft Drinks
• Set Menu Dinner
• Fine Cuisine
• Al Fresco Dining

If you have any specific dietary requirements whilst on-board your cruise, you can add this to your special requests on step 2 of the booking form. We advise limiting these requests to religious beliefs or food allergies.

Languages Spoken

The crew speaks English.

Accommodation

Master Stateroom

Guest Staterooms

Boat specifications.

• Year built 1990
• Year renovated 2018
• Length 72'
• Beam 18'
• Top speed 9 knots
• Cruising speed 8 knots
• Engines twin 150hp
• Max guests 6
• Number of cabins 3
• Number of bathrooms 3
• Tenders 14'
• Water capacity 800 gallons
• Fuel capacity 600 gallons
• Freshwater maker yes

Boat Navigation and Safety

• Depth Sounder
• Radio VHF/DSC/SSB
• E.P.I.R.B. Distress System
• Fire Alarm & Fire Extinguishers
• Satellite & mobile phones
• Bilge pump alarm
• Search light
• Engine room CCTV
• Crew trained in first aid
• Emergency flares

We’re here to help, 24/7.

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Gear Rental

There is equipment available to rent on this boat. Please provide your rental needs on the booking form. You will need to pay for the rental gear on board of the boat.

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• 1 double bed
• Aircon with control
• Ensuite Bathroom
• Max 2 guests

The Master stateroom is a private beautiful place to call home for your charter. It boasts a king-size bed, a small couch, vanity or desk area and a private bathroom with shower and bathtub. There is ample storage for all your clothes and adventuring gear in 12 draws and one hanging closet. This room offers reading lights, a fan, two large hatches in the ceiling and four portholes, this gives the room a lot of natural light and gives you the opportunity to see whales right from your bed!

Gypsy Wind offers two guest staterooms. Both of the guest staterooms are the same offering full-size beds, private bathrooms with showers and ample clothing storage. They both have 6 draws and a hanging closet to store all your clothes and adventuring gear. There are reading lights and a fan to keep you comfortable.

Rental Gear Prices

FLEXIBLE BOOKING – This liveaboard offers a free trip reschedule within 24 months if you are unable to travel due to Covid-19 related restrictions.

If you wish to cancel instead of reschedule then the following cancellation terms apply;

• More than 90 days out = 90 % refund
• Between 30 and 90 days out = 75 % refund
• Less than 30 days out = no refund
• The destination country prevents you from entering due to their governmental guidelines and restrictions on your country of residence.
• Your country of residence prevents you from departing due to their governmental guidelines and restrictions on the embarkation point for the liveaboard.

Only if one or more of the above apply, this liveaboard operator will offer a free re-schedule of your trip within 24 months from the initial departure date

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Gypsy Wind Charters

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Gypsy Wind Charters - All You Need to Know BEFORE You Go (2024)

Gypsy Wind Charters

Rates and Dates

Yacht Description

Gypsy Wind yacht is a 72.00 ft long sailboat monohull and spends the summer in Alaska. It was built by Irwin in 1990. A refit was done in 2018. The yacht layout features 3 cabins and accommodates 6 guests. The cabin arrangement is following: 1 king cabin, 2 queen cabins, 1 pullman cabin.

The sailboat features twin Yanmar 150hp main engines, Northern lights 20kw generator. engines and a generator.

Accommodation

Weekly price low-high season

Price Details

Price from: €22,000

High season rate: $22,000

Rates are all inclusive except for alcohol.

Specifications

More Specifications

Water sports, other entertainment.

External hard drive with over 400 movies.

Crew Information

Captain: Jonathan Yoors

Captain Jonathan Yoors Jonathan is originally from Rockport Massachusetts, a small fishing village an hour north of Boston. He has captained boats all over the world but his favorite place to sail and spend time is in the Caribbean and Alaska. Jonathan is a USCG 500ton captain with over 11 years yachting experience and 15 years owning and captaining his own boats, you can rest assured knowing you have an experienced captain at the helm. Jonathan loves to fish, spear fish, snorkel, hike, kayak, paddle board, explore the wilderness and enjoy all types of nature and wildlife the Caribbean and Alaska has to offer. Chef Brittany Battistoni Brittany is originally a southern California native with a love of traveling the world. She is a professionally trained chef with nearly 15 years professional food service experience. She is also an avid naturalist and enjoys opening the minds of those around her by taking them foraging for local wild edibles in the areas she is on charter in. Brittany is very passionate about food, the environment, critter watching, kayaking, paddle boarding, spear fishing, snorkeling, and other water sports. You can expect to enjoy exceptional locally caught food while chartering GYPSY WIND. Jonathan and Brittany are a married couple who have been exploring the world together for 7 years now. They have sailed around the east coast of the US and the Caribbean for 3 years, cruised Alaska for 4 years, and sailed across the Atlantic. They both share a love of adventure and a deep love for nature.

Mixed green salad with balsamic vinaigrette

Angle hair bolognaise, garlic bread.

Flourless chocolate cake with raspberry coulis and whip cream.

Eggs any style with toast and bacon.

Curry chicken salad over a bed of greens served with pita.

Whole roasted side of Hawaiian marinated salmon, green beans with cranberries and almond slivers, steamed rice.

Pineapple upside down cake with vanilla ice cream. 

Pancakes with fruit and breakfast sausage.

Halibut fish tacos, refried beans, chips and salsa.

Chicken burre blanc, broccoli, and crispy roasted potatoes.

Chocolate mousse with berries and whip cream.

Veggie Frittata served with fruit.

Crab or Chicken Quesadillas served with a chopped salad and a citrus vinaigrette.

Halibut Picata, steamed Brown rice, and a shredded vegetable medley.

Cheese cake pie served with Berry compote.

French Toast with maple syrup, and bacon.

Teriyaki pulled pork bowls with rice and shredded veggies.

Chopped salad, tomato, cucumber, peppers, olives, onion, feta cheese, and a white wine vinaigrette.

Grilled Ribeye, brown sugar butter glazed sweet potatoes, and brussels sprouts in a bacon cream sauce.

Wild berry cobbler with vanilla ice cream.

Quiche Loraine with fresh fruit.

Your choice of Artisanal pizzas! Peperoni, cheese, smoked salmon with pesto, artichoke hearts and fetta, or sausage pepper and onion.

Roasted root vegetables, and cous cous salad. Dungeness crab with drawn butter and lemon.

Key lime pie

Build your own Belgian waffles, blueberry, chocolate chip, banana, whip cream, maple syrup, breakfast sausage.

Seafood chowder, Freshly made biscuits. 

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GYPSY WIND Yacht for Sale

68' irwin | 1990 | $379,000.

• Yachts for sale
• express cruisers

Last updated Jan 25, 2024

Gypsy Wind Boat | 68' Irwin 1990

This highly customized Irwin 68 was completed in 1990 to a much higher construction specification than standard sister ship designs. Earl Blackwell, Jones & Associates, specialists in manufacturing process and design engineering, specified and blueprinted to a heavier hull and deck laminate that meet the National American Bureau of Shipping (ABS) standard. The result was an exceptionally strong Irwin that is well suited for offshore or island cruising. She is in great shape with tons up upgrades and work done in the past 4 years. Safe, comfortable and fast. She has a master stateroom after with fulll head and bath tub, two full size staterooms just forward of the master each with full head. Main salon is huge with a wet bar, ice maker, big table that seats 8 comfortably. The galley is just forward and to starboard of the salon with two refrigerator freezer, 4 burner propane stove with oven, large sink, and lots of storage. Across from the galley is the utility room with tool storage, food storage and a newer washer dryer unit. Forward of is the crew area with tow bunks a large V birth and a shared head.  On deck she is large and safe. She has all the navigation equipment you need including newer Garmin gps with radar, new raymarine wind instrument independent depth sounder raymarine autopilot with new hydraulic pump in 18 and rebuilt hydraulic ram in 2019, 2 vhf radios one with AIS receiver. On the aft deck she has a large hot tub with new cover, large lazarett for storage, smoker/ bbq, 2 chest freezers, dinghy davit with solar mounted above. She has a custom built hard top designed and installed by Ted Irwin with 2 large solar panels on top.  She has been lovingly updated and upgraded by her current owners and below is a list of all of these upgrades.  600 gallons of fuel 800 gallons of water 35 gallon holding tank currently setup as a charter boat in Alaska, can sell the business or just the boat. also comes with a 14' Ted Irwin fiberglass tender with a 25hp Yamaha four stroke engine.  Owner awaiting offers.                     

Denison Yachting is pleased to assist you in the purchase of this vessel. This boat is centrally listed by Fairhaven Yacht Sales.

Denison Yacht Sales offers the details of this yacht in good faith but can’t guarantee the accuracy of this information nor warrant the condition of this boat for sale. This yacht for sale is offered subject to prior sale, price change, or withdrawal from that yacht market without notice. She is offered as a convenience by this yacht broker to its clients and is not intended to convey direct representation of a specific yacht for sale.

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Gypsy Wind HIGHLIGHTS

• Yacht Details: 68' Irwin 1990
• Location: La Conner, WA
• Last Updated: Jan 25, 2024
• Asking Price: $379,000

Gypsy Wind additional information

• Beam: 17' 2''
• Hull Material: Fiberglass

1990 Irwin Pilothouse Ketch This highly customized Irwin 68 was completed in 1990 to a much higher construction specification than her sister ships designs. Earl Blackwell, Jones & Associates, specialists in manufacturing process and design engineering, specified and blueprinted to a heavier hull and deck laminate that meets the National American Bureau of Shipping (ABS) standard. The result was an exceptionally strong Irwin that is well suited for offshore or island cruising. She is a rare twin engine Irwin. One engine is a Yanmar 4LH- DTE and one is a Yanmar 4LH-HTE. Both main engines have four bladed folding props and two fixed spare props are onboard. One of her powerful main engines can push her to a comfortable cruise of 8 knots while the other engine sits ready to go as a backup. Both engine have newer injectors and new turbos. She has a electric bow thruster by Vetus with its own battery system and charger (new 2016). The electrical system has been upgrade in the past 2 years. Brand new Phazor 15kw generator in a sound shield gives you all the power you could want. When not running the generator she can run off of her 14 golf cart house battery bank (new 2022) with help from 2 Victron multi plus 3000 watt inverters you can run everything very comfortably. All of the battery supply wiring is new including new battery switches, fuses, bus bars and Victron monitoring system. When you house batteries get low you can charge them via the 1270 watts of solar or via the inverters giving 230 amps of charge or via the main engines. Each main engines alternator directly charges the house batteries and each engine has a dedicated start battery that is kept fully charged by a new DC to DC charger ( 2 Victron 18amp). All the lights are Led to help save power.

Water is supplied by two 400 gallon tanks with valves to select one tank or both tanks to feed the water pump. The Spectra Cape Horn Extreme is a large DC water maker with Energy recovery system. Run one or two boost pumps and make 7 or 18 GPH. Hot water is supplied by a new 20 gallon hot water tank that is heated by 120v or the strb main engine. There is also a newer propane instant hot water system. ( Shower mate by precision temp) The four heads onboard are electric heads (2 brand new). She is in great shape with tons up upgrades and work done in the past 4 years. Safe, comfortable and fast. She has a master stateroom after with full head and bath tub, two full size staterooms just forward of the master each with full head. Main salon with a wet bar, ice maker, big table that seats 8 comfortably. The galley is just forward and to starboard of the salon with two refrigerator freezers, 4 burner propane stove with oven, large sink, and lots of storage. Across from the galley is the utility room with tool storage, food storage and a newer washer dryer unit. Forward of is the crew area with tow bunks a large V birth and a shared head. On deck she is large and safe. She has all the navigation equipment you need including newer Garmin gps with radar, new raymarine wind instrument independent depth sounder raymarine autopilot with new hydraulic pump (2018) and rebuilt hydraulic ram (2019), 2 vhf radios one with AIS receiver. On the aft deck she has a large hot tub with new cover, large lazarett for storage, smoker/ bbq, 2 chest freezers, dinghy davit with solar mounted above. She has a custom built hard top designed and installed by Ted Irwin with 2 large solar panels on top. She has been lovingly updated and upgraded by her current owners and below is a list of all of these upgrades.

600 gallons of fuel range on engine of aprox 1500nm 800 gallons of water 35 gallon holding tank Currently setup as a charter boat in Alaska, can sell the business or just the boat. Comes with a 14' Ted Irwin fiberglass tender with a 25hp Yamaha four stroke engine, a 2 person kayak, lots of extra parts and tools.

Upgrades to Gypsy Wind

1. Two 305-watt solar panels installed on aft davit : 2. Outback Solar Mppt 80amp charge controller :  3. A/C raw water pump  : 4. New broiler in oven  :  $100 5. TV  :  $200 6. Fans in all guest rooms  :   7. All new fire extinguishers  :  8. EPIRB  :  9. Both fuel tanks polished  :  

1. New Genoa chain plate and stay sail chain plate.  :  

1. Cutlass bearings 2. PSS shaft seals 3. Pulled both shafts dialed them 4. Pulled all 4 shaft struts and rebuilt them and reinstalled 5. New rudder bearing and all new bolts 6. New thru hull galley 7. New bottom paint  :     8. 400 feet ½ BBB chain for main anchor  :  9. Victron Multi plus 3000 inverter / charger in salon  :  10. Washer Dryer  :   11. New injectors on both main engines  :  12. Precision temp instant hot water :  

1. Engine mounts on both main engines  :  2. Tank tender for water tanks  :   3. Alternator on both engines  : 4. Head faucets all guest rooms  :  5. New paint on house outside and new non skid on decks  :   6. Two 330 watt solar panels on hard top  :    7. Victron MPPT solar charge controller  :   8. DC water pump  :  9. 2 coats new bottom paint  :  10. 4 new custom made mattresses  :  11. 15 KW Phasor generator in sound shield  :    12. New Clarke Pump on water maker  :   13. All new DC power supply wires, fuses, battery switches  : 14. Victron DC to DC chargers for both engine start batteries  :  

1.  Victron Multi Plus 3000 in bow  :  

2.  14 new lead acid 6V golf cart batteries    :  

3. All new upholstery in cockpit, salon, and master  :  4. New main sail  :   5. New chain plates on the outside of the hull  :  6. Rebuilt in mast roller furling main sail system 7. Bottom paint 8. New turbo on both main engines 9. Valve adjustment both main engines 10. New back stay 11. New staysail stay 12. All new Marelon thru hulls 13. New 20 gallon Raritain hot water tank 14. New Mizzen sail 

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Becoming Captain: Living A Dream In The Virgin Islands

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• Gary Waleik

Coy Theobalt was first enchanted by the open sea when he was 8 years old. After a fishing trip with his father, Theobalt says he made up his mind: He wanted to become a boat captain.

But it wasn't until years later that Theobalt actually became " The  Captain."

After 17 years of work in therapy and counseling, Theobalt was tired of working in an office. He took his corporate leadership development practice to the field (and ocean), guiding outdoor excursions, boating trips and more.

On one visit to St. Thomas in the spring of 2005, Theobalt found his calling.

"I was standing at a gas dock about to pay my gasoline bill for the boat, and I picked up this little island rag and opened it up, and there was this boat and this business, and everything just spoke to me right then," Theobalt says. "I just looked at that and said, 'I think that's my boat.'"

By November, the move from Colorado to the U.S. Virgin Islands was complete. But adjustment to island life took some time.

"When people come to the islands, you're either gonna have to slow down or you'll go crazy," Theobalt says.

When he finally got his new charter sailing business off the ground, Theobalt had found peace.

"Just sitting in the cockpit and leaning back and looking at the sky and looking at the clouds, and the water, and the sun, and just saying, 'Wow, this is my new life, and I love it,'" he says.

His business flourished ... at first.

But on one trip through the Caribbean, Theobalt — and his boat — were in danger.

"It was one of the most terrifying 25, 30 minutes of my life," he says.

Click the play button next to the headline at the top of the page to hear the full story. And learn  more about Coy Theobalt's life as a charter captain in St. Thomas in his book " Gypsy Wind Speaks ."

This segment aired on January 14, 2017.

• Erden Eruc: The Man Who Rowed Around The World

Gary Waleik Producer, Only A Game Gary Waleik is a producer for Only A Game.

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• By Michael Robertson
• Updated: June 8, 2012

Before kids, Windy and I cruised aboard the first Del Viento for seven months through nine countries without once using a windlass to manage our ground tackle. This makes sense, as we didn’t have a windlass. We spent 95 percent of our nights at anchor and I routinely lowered and retrieved our 22-pound Bruce attached to 125 feet of quarter-inch chain and 200 feet of half-inch three-strand. I would open the anchor locker on deck, don gloves, and sit with my feet braced against the pulpit bases. Sometimes Windy assumed this role. It was a simple, straightforward approach that worked every time.

Aboard the new Del Viento , things aren’t the same. Our Bruce is three times as heavy and instead of being attached to 91 pounds of chain, it is attached to 465 pounds of chain. We rely on our windlass and it is usually Windy who operates it.

Her work begins before we reach an anchorage, removing the retaining bolt that secures our 66-pound Bruce on the starboard roller. As we get closer, she turns on the windlass breaker down below. She doesn’t bother with gloves. When we agree on a suitable spot, I report the depth. She pulls a foot of chain up from the locker to create slack and then coaxes the anchor halfway off the end of the roller so it is ready to fall.

Then everyone on board takes a deep breath because shortly after she begins to lower the anchor, things often go bad.

The first time the chain jumped the gypsy, 30 feet or so ran out over the top before it caught, jerking the windlass so violently we both thought the next time may result in a giant hole on deck and a windlass on the bottom.

Three-eighth-inch chain pulled out-of-control over the top of a gypsy by a falling 66-pound anchor is loud and unsettling, and potentially dangerous. Until the anchor hits bottom, the forces multiply as more chain runs out, speeding everything up.

The chain appeared sized correctly to the gypsy, but the anchor roller was proud relative to the gypsy and we weren’t getting the recommended 90 degrees of contact. I had a carpenter in Puerto Vallarta make a 5-inch-tall base of hardwood on which I mounted our windlass on deck. We were still not getting the contact we needed, so I had a stainless guy in La Cruz make a second anchor roller that drops the chain four inches. These modifications put a lot more chain on the gypsy and were sure to solve our problem.

Nope. Whether we lowered the anchor with the windlass, or eased the clutch to let it fall, it would usually jump at some point. Fortunately, we weren’t anchoring often at this time.

Never having owned or used a windlass before, we talked to the former owners of Del Viento . They were familiar with the problem, but always kept a foot pressed down over the top of the gypsy to prevent the chain from jumping. Windy started wearing shoes, but was uneasy with this solution. Restraining the chain with a part of her body didn’t feel safe.

And the chain didn’t jump every time or under specific circumstances. Sometimes Windy would raise and lower the anchor three times in a row without incident and her comfort level would begin to rise…until it would happen again.

The night before we sailed into La Paz was the worst. There was a lot of chop in the anchorage and the wind was up. Windy went forward and began her routine. The anchor went down but didn’t set. She’d nearly raised it to try again when the chain jumped and ran over the top of the gypsy. Then, for the first time, the runaway chain left the gypsy. We both thought the sound of chain running over the top of the gypsy was bad; now we knew it could get much worse. This time the runaway chain ground a chain-sized gash into the corner of the hardwood block onto which our windlass is mounted. Fortunately, the chain stayed on the roller.

In La Paz, I added a larger, three-quarter-inch polyethylene windlass backing plate below decks to mitigate the damage we feared may happen. And we again asked several folks their opinion:

“Does this gypsy look sized correctly to this chain?” “Could our chain be stretched?” “Does our gypsy look worn to you?”

Our windlass is at least 20 years old, a Lofrans Cayman. The folks at Imtra are helpful, and they know windlasses, but they know nothing about our old model. They said they have no drawing, specs, parts references, nothing. We emailed back and forth, trying to troubleshoot. I sent pictures and descriptions. The Imtra consensus was that our bronze gypsy was worn. They had replacements, but they were for newer models and they couldn’t assure me they would fit. With tax and shipping, we were looking at $300 for a new gypsy.

I took our unreliable gypsy off the boat and put it in our rental car. Out and about, I began asking everyone in San Diego their opinion. The old salt who runs a chandlery and sells windlasses opined that my gypsy was fine. A self-professed windlass expert at Downwind Marine said mine looked worn. A couple yard workers weighed in with varying opinions. The customer service desk at Trader Joes said they’d never seen a gypsy nor a windlass. I took the $300 plunge.

The new gypsy fits our old Cayman, but is different. The shoulders that border the chain link pockets are broader and taller, forming a much narrower channel for the link that rests vertically, I think mostly by design and partly because of lack of wear. Windy conducted testing here in the slip and she’s elated with the results. Once we even saw the chain emerge from the locker with a twist, yet it seated itself perfectly in the new gypsy.

Here is the same chain sitting in our old gypsy. Note the red arrow pointing at the shoulder for the vertically oriented link. The cutaway angle you see begins lower in the pocket than _on the new gypsy and creates a much wider gap between __links, leading to the jumping. Some of these shoulders_ _were a bit more worn than others, resulting in the_ _inconsistency._

This episode is especially gratifying because the windlass (along with booms and winches) is a piece of equipment on board with the potential to be the source of severe injury to crew. Now that anchoring will be safer aboard Del Viento , I may give Windy a break and take my turn on the foredeck.

_I__n our twenties, we traded our boat for a house and our freedom for careers. In our thirties, we slumbered through the American dream. In our forties, we woke and traded our house for a boat and our careers for freedom. And here we are. Follow along at _

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Exquisite Accommodations and Your Own Fishing Boat!

30 steps to the gulf of mexico, ​​3 master suites with king beds & en suites, three story elevator, two sets of washers & dryers, heated saltwater pool with tiki bar and outdoor shower, gourmet kitchen, two large screened-in, wrap-around po rches with jacuzzi, full-home clean water system, two 6-person golf carts, 10' bote float , 4 kayaks, 3 sups, beach cruiser bikes, & so much more.

Your Island

For Your Island Vacation

*Use of the boat is conditional on boating experience. Insurance, Fuel, cleaning fee, and any equipment rentals is an extra fee.

Recent Guest Reviews

Jill A.  September 20 2 3

Our week here at Gypsy Wind has been nothing short of spectacular. I could (and will) go on and on, so hang in there for a full review! First, I was nervous about staying on an island, worrying it would feel too remote. I was also concerned about staying on an island hit by a hurricane less than a year ago. After fighting my fears and coming anyway, my worries were for naught (as they usually are, right?). With some preplanning for food and other essentials, we’ve had everything we needed. And, when I needed brown sugar for spontaneous cookie baking, Kale (property manager) posted it on the local owners' page; I had two bags of brown sugar at my door in less than 15 minutes! The locals and other guests were all so friendly. Kale is at your service for anything you need, 24/7, which eased my overall concerns. The boat ride from the mainland is less than 30 minutes long, and the water is shallow - mainly 4 feet deep! In addition, North Captiva has medics, a fire department, and a helicopter if there is an emergency. I felt safe here. And, though parts of the island are still recovering from the hurricane, it has not taken away from the experience at Gypsy Wind nor on North Captiva Island. Gypsy Wind’s location is an ideal spot on the island, private and only a stone’s throw away from the beach. The Gulf and sunset views are incredible! The beach is “sugar sand,” white and clean, with more shells than I have seen elsewhere. Unlike many other homes on the island, G.W. is a beachfront property. Also, I learned how lucky we are to have rented a completely screened-in place. Florida beaches have little bugs called “noseeums,” we weren’t bothered by them while dining on the porches, drinking coffee on the swing, etc. The house itself is luxurious and comfortable, all in one. The three levels are tiled with cozy furniture and throw rugs. The cleanliness is impeccable, and the decor is so tasteful! I am ordering some of the things for my home. The beds are incredibly comfortable, as is the bedding. The rooms are zoned for air conditioning, the bathrooms have bidets, the showers are perfect, and the kitchen is fully equipped, better than our home! Everything I needed to cook for a crowd was here: cookie trays, crock pot, Keurig/coffee pot/Espresso-Latte machine, and enough pots, pans, dishes, glasses, etc. for many! The internet is high-speed, the TV and movie screen are a plus, and there are puzzles and games for rainy days. The beach walks are incredible with shelling, fishing, sand castle building, and a new, extra large party float for guest use that arrived during our stay! The 6 of us hung out in it in the gulf! There are also paddleboards and kayaks. You can also rent their boat. Kale will teach you how to use it. We went to Cayo, a 10-minute ride from here, and did some incredible shelling, including sand dollars! Aside from beach activities, there are several outdoor things to do right at the house, including the pool, Tiki bar, corn hole, Foosball, Ladder Toss, and more! My favorite place to be is on the swinging queen-sized day bed! I went there when I needed a little space from the family and for the Gulf view. We have enjoyed touring the island on the golf cart, visiting manatees, a local swim bar/eatery (Mangos), a gift shop, and getting ice cream! While there are other rentals on the island, we learned while staying here there were extra amenities other rentals don’t offer: transportation to and from the island, boat/dock access, pool, hot tub, two golf carts, screened-in porches, outdoor day bed, and the floating dock with anchor. The organized website helped us be best prepared - be sure to check it out. We did have questions ahead of time, and Linda and Jim were helpful and eased my worries. We don’t want to leave; we will be back! Just do it!

Cheryl H.  August 20 2 3

Not even sure where to start! We recently had our family vacation and were lucky enough to stay at Gypsy Wind! This was our second time visiting North Captiva and it was even more magical! From the ease of ordering food, to the seamless pick up at the dock and arrival at the home to the service throughout the week… we could have not asked for more.

The house was spectacular and large enough for all of us to gather comfortably or space out as needed! Jim and Linda were so responsive from time of booking to our departure from the house despite dealing with a hurricane in between. Our house was expertly stocked by Antoine and Cale was there all week to answer any questions that we had. We also had a wonderful dinner prepared by Chef Bo. If you are looking to get away from it all, but at the same time enjoy all the comforts of home (and more!) this is the house for you. We look forward to coming back again and again.

Heidi W.  June 20 2 3

Just returned from a week at Gypsy Wind retreat in North Captiva and a 5 star scale doesn’t come close to measuring the incredible time we spent there!! If you are looking for total relaxation in a top shelf environment you can’t do better than Gypsy Wind. From the owner and property manager communication prior to our travel, to our flawless arrival, they delivered. Antoine Good from. A Good Grocery did our shopping and our order was perfect! The home is impeccably appointed with everything from an elevator to 2 new six passenger golf carts, Viking appliances and a warming drawer in the chef’s kitchen, two sets of washers and dryers (with environmentally friendly ozone system!!) located on pool and living room level respectively as well as refrigerators to accommodate groceries and libations for all your guests!! With 4 huge rooms 3 with en-suite bathrooms) plus a bunk room for the kiddos, 2nd floor hot tub and coffee bar for watching the sunset over the water, smart toilets, spacious bedrooms, bathrooms, board and yard games, 2 kayaks, stand up paddle boards, and pool toys galore you family won’t think about phones, meetings or video games because there is something to do every moment of your stay. Not to mention the entire house smells like a 5 star hotel spa!! We fished, swam, snorkeled, hunted for shells, island hopped, had game and movie nights and saw all kinds of local wildlife (box turtles, rabbits, manatees, tarpon and dolphins, osprey nests, and pelicans) as we explored the island. Most of these could be seen from our 2nd and 3rd floor screened porch overlooking the Gulf of Mexico. There is nothing missing from this home. Handcrafted soap, tropical breezes and the most beautiful sunsets you will see anywhere. Every tool, accessory and cooking implement (and grill) you can think of is here. Both the owners and property manager were accessible anytime we had questions no matter how small. If you are ready for the vacation of a lifetime without the need for a passport- book your stay at Gypsy Wind. You won’t ever want to leave!!

What is a Gypsy Wind ?

A nautical expression for a sailing vessel stocked to the brim with culinary treats for creating stimulating conversation and providing memorable times with special guests.  it also refers to a breeze that swirls and varies in speed and direction as if it follows no rules or customs. ​ the two meanings wonderfully intertwine to capture the atmosphere of our island beach home.  a place to entertain guests and enjoy the island life at your own leisurely pace. we want our guests to know, that when you arrive, we will be stocked to the brim with everything your family and friends need to enjoy this wonderful island paradise., bob seger referenced gypsy wind in his song,   "you'll accomp'ny me"   "a gypsy wind is blowing warm tonight the sky is starlit and the time is right and still you're tellin' me you have to go before you leave there's something you should know...".

Rent the Ultimate Fishing Machine for SWFL, DORADO 23

Luxury Beach home with fishing boat allows renters of Gyspy Wind to rent this fully-outfitted fishing boat during their vacation stay at the luxury island home. Interested in renting the boat for your stay on North Cap Island? Click the REQUEST button for more details.

Gypsy Wind Boat Rental

Beginning the summer of 2023.

Guests staying at Gypsy Wind may now rent our 23' semi-custom center console . Either bareboat (if you have experience) or have Captain Kale show you the exceptional waters off North Cap.

​Our weekly rental terms allow qualified renters to fish up to twelve miles offshore ; no other rental boat in the area allows that range. That lets you reach plenty of great reefs and structures and our SIMRAD electronics has more waypoints than you could fish in an entire summer. We also offer a variety of rods, reels, and tackle to help you land your target species.

This semi-custom center console, built a short drive north in Bradenton, epitomizes the design challenges of successfully navigating the waters of southwest Florida. Run shallow while providing a dry and comfortable ride. Pine Island Sound chop can deliver a pounding on windy days, but Gypsy Wind cuts thru it with a Carolina flare bow. 

Our 23-foot Dorado center console fishing boat is the best in the market, outfitted with top-of-the-line electronic fishfinding technology and the best fishing gear and accessories money can buy. You can rent our boat and enjoy a luxurious fishing adventure with your friends and family.