What we're about

Though we are located in Connecticut, we offer opportunities for travel via private yachts all over the world with professional captain(s).

You do not have to have sailing/boating experience!

Spots are sold by the cabin or as a single.

We venture to places like Greece, Grenadines, Cuba, British Virgin Islands, Croatia, Bahamas.

Interested in learning more about sailing? Would you like to take the helm? Would you like to sit back, relax, read a book while the coast goes by? All of it is ok! All we ask is you bring your curiosity and laughter aboard.

Again, you do not have to be local to participate. Our sails originate all over the world.

Upcoming events (3)

British VI 10 day sail! 2 boats October 21' FULL

Road Town

Flex booking.

10 days sailing these lovely islands this October!
Our boats will sail in tandem.

One spot on catamaran is a share with female. The other is private cabin on brand new 47' monohull, with lots of space.
Step aboard October 21st. Sleep aboard at dock. The next day, after the inspection and briefing, we will be off sailing! Stops include places like Cooper Island, Jost van Dyke, Little Jost, Virgin Gorda, Trellis Bay, Norman Island to name a few.
Explore these islands as they were meant to be explored, by sailboat.

Sit back and relax or get involved in sailing. No experience necessary, just a thirst for adventure and exploring all these islands have to offer, is all that's required. Of course we love people eager to learn and would really appreciate it!

We will practice covid protocols with masks, sanitizing etc.

Come with a friend, family or by yourself. All welcome. (singles will be matched with same sex in cabin or choose private cabin)

$1900 per person based on double occ. Single cabin $2100 (monohull)

Here is what is included:

Captain
9 night accommodations on board.
Breakfasts, some lunches and dinners aboard
Safety, Navigational Aids
Galley Equipment
Bed Linens and towels
Basic Paper Products and Essentials
End Cleaning
Dock and Port Fees and boat Taxes
Parks permits for BVI
Cruising permits for BVI
Vessel insurance
Damage Waiver Insurance

Prices DO NOT INCLUDE:
Airfare
Boat kitty $150 for moorings, dockage
Land accommodations
Personal Travel Insurance (recommended)
Meals in restaurants
Provisioning – specialty foods and alcohol
Additional land excursions
Snorkel gear
Flying into STT instead of Roadtown, better connections. Ferry to Roadtown and cab to boat. Easy!

Message me or text Capt. Joy with any questions[masked] or to obtain registration form. NOTE- signing up here does not automatically put you on a boat. We have to have an interview on the phone or zoom.

Thailand Sail 2022 January 15-22nd Private double cabin available!

2022 dates of sailing portion Jan 15-22, 2022
Arrive Jan 11th or 12th for a few days on the beach. Board our boats for a week of sailing then fly to Bangkok for a few days.
Our own private luxury catamarans will be our home for a week of exploring the magnificent islands of the Andaman Sea.
Over 130 islands to explore, emerald waters, secluded beaches. Southeast of Phuket brings you to the Phi Phi Islands – one of southern Thailand’s favorite tourist destinations. Cliffs rise dramatically from the sea. Stunning overnight anchorages and charming villages offer unique lunchtime stops and incredible nightlife. Many of the islands in this region are surrounded with dazzling coral reefs so rich in marine life that you will be tempted to spend all of your time in the water.
per person (dbl occupancy)
Sailing experience not necessary! Smiles and humor are always welcome.
Everyone shares the cooking.
World class diving and snorkeling await!
We've sold over 14 spots. Don't wait on this one!
Price per person (double occupancy) $2180

Price includes:
7 night accommodations on board in a double occupancy cabin
Food and water provisioning for all breakfasts, some lunches and two dinners onboard (the rest of the meals will be ashore)
Safety, Navigational Aids
Fuel and water along the way and upon vessel return
Galley Equipment
Bed Linens and towels
Basic Paper Products and Essentials
End Cleaning
Dock and Port Fees and boat Taxes
Vessel insurance
Damage Waiver Insurance

Prices DO NOT INCLUDE:
Airfare
Land accommodations
Personal Travel Insurance
Meals in restaurants
Provisioning – specialty foods and alcohol
Additional land excursions

The plan is to arrive in Phuket a couple of days before our sail. After our sail it would be your option to inter fly to Bangkok for a few more days of touring, maybe side trip to Chaing Mai before flying home. This would be on your own. Flights from Phuket are less than $100. Overnight train to Chaing Mai. Firm itinerary will be set later.
Hotels and food incredibly reasonable!

If you want to come along. Your deposit of $500 is required to hold your spot.
Less than 30 day stay, no visa requirements.

South Cuba Sail and Land Excursions March 2022

Update - holding off on securing this trip until we have more information on Covid 19 status. Dates are approximate.

Hello Sailing Collective!
This sail has just been announced on a few platforms. I expect it will fill. Contact me if you have additional questions. Anyone who signs up we'll have some time to talk on the phone.
I have organized and captained over 25 sailing charters. (you're in good hands!)

We're heading back to Cuba!

This will be my fourth trip to Cuba. We have partnered with an educational tour agency that specializes in Cuba by land. They are full compliance with OFAC regulations. We know what to expect both navigating the waters and on land. This opportunity is so special, I want to share it with you!
The lovely people of the Cuba the pristine beauty of the Southern Cuba islands, are not to be missed. If Cuba has been on your bucket list, now is the time.
You do not have to have sailing experience to join us.
We will call home for our week a 45' Lagoon catamaran with all the bells and super comfortable.
This is a rough itinerary and is subject to updates and changes.

Cuba is a hidden gem. The architecture, the infrastructure, the culture, and of course, the cars - all feel like a stroll up memory lane. Captain Joy is offering a rare (and maybe even once in a life time) opportunity to explore Cuba before it changes forever.
Welcome aboard!
Catamaran, Lagoon
Shared double bed with private bathroom.
Includes breakfasts, lunches and one dinner

SEA ITINERARY $based on double occupancy
This is a rough itinerary and is subject to updates and changes.
Sat Nov 10: 5pm Embarkation - Cienfuegos
Sun Nov 11: Cienfuegos – Cayo Guano del Este
Mon Nov 12: Cayo Guano del Este - Playa Sirena – Cayo largo
Tue Nov 13: Cayo Largo – Cayo Cantiles
Wed Nov 14: Cayo Cantiles - Estopa Canal – Cayo Rico - Cayo Largo
Thus Nov 15: Cayo Largo – Ballanetos– Cayo Sal
Fri Nov 16: Cayo Sal - Cienfuegos
Sat Nov 17: Disembarkation

LAND ITINERARY Add'l $
Includes round trip pick up and drop off to airport. Includes your visa.
All breakfasts, lunches and 2 dinners included.
Nov 8 HAVANA
All day Arrivals
Check- in to casas and welcome drinks and orientation, money exchange
Welcome Dinner (included) at Paladar San Cristobal (where Obama had dinner)
9 pm – welcoming event at FAC (Fabrica de Arte Cubano) You won’t want to miss this!

Nov 9 HEMINGWAY HOUSE then travel to TRINIDAD
9 – 10am Breakfast at casa
Morning: Visit to Finca Vigia – Hemingway house
Visit to Muraleando community project
Lunch (included) with Muraleando community
Afternoon: Drive to Trinidad
Evening: Dinner on your own
Cocktails at the cave bar Disco Ayala (optional)

Nov 10 TRINIDAD /CIENFUEGOS
9-10am Breakfast at casa
Morning: Tour of Trinidad - history, Santeria religion, architecture
Afternoon: Drive to Cienfuegos – lunch (included) in Finca on the way
Tour of Punta Gorda in Cienfuegos and Main Plaza
Evening: 5 pm – Boarding on boats.
One week sail
Nov 17 HAVANA
Morning: Transfer to Havana – lunch on road.
Afternoon: Classic car ride via Revolution square, Havana Forest, Malecon etc
Evening: Dinner on your own

Nov 18 Some will depart for USA

Additional tour option $150
Nov 18 LAS TERRAZAS - visit to eco - community
8 -9 AM Breakfast at casa
Morning: Drive and Tour Las Terrazas, eco-community of artists, coffee growers, etc.
Lunch (included) at Las Terrazas - Campesinos farm -
Afternoon: Visit artist studios, then coffee tasting, discussion with Cuban coffee industry.
Visit to spectacular Hotel Moka. Go for a swim in baños
Evening: Havana – Dinner on our own.

Nov 19 Departures

Prices DO NOT INCLUDE:
Airfare
Personal Travel Insurance - recommended
Meals in restaurants
Provisioning – specialty foods and alcohol
Additional land excursions not listed here.
Must sign travel waiver.
We will be bringing your donations to a local charity.
$500 deposit with registration form due now. (message me for details)

Past events (29)

SAILING On Sale! Monday Sunset! Great weather.

63 Pilots Point Dr

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