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Vieques Sailing

with Capt. Tom Kirkbright

So you thought this day would  never come, but finally you made it, on vacation in a beautiful tropical paradise. You have planned well;  a Bio-bay excursion, maybe a trip  to the Fort Conde de Mirasol,  a guided Sugar Mill tour or a few days just relaxing on the beach.  There are endless opportunities to keep you and yours entertained on Vieques. But maybe you’re looking for something special, hands on, exhilarating, a highlight to your visit. That’s an easy fix. It’s a day spent “On The Water”.  Let Vieques Insider guide you through the options.


The trade winds propel you through the clear pristine water.  The sounds of birds, the wind filling sails and water lapping off the hull are clear and unencumbered.  The gentle roll brings you to that place where all the stress of daily life washes off in the breeze.  It’s time to go sailing.

Caribbean Lady Sailing Charters offers group and private full day charters from Esperanza on a 47’ Beneteau Oceanic Sloop.  Departing at 10 am, 11 am for sunset, the Caribbean Lady returns at 4 pm or 5 pm, respectively.  Depending on wind direction she sails east to the open water reefs of Blue Tang off Cayo La Chiva, or Lemmon at Ensonada Honda, both offering incredible snorkeling, or west off the beautiful beaches and reef at Punta Areas.

  1. Food – fresh fruit and veggie appetizers while underway –complete sandwich buffet with vegetarian and gluten free options and homemade desserts while at anchor

  2. Beverage – water, soda, juice, beer and rum punch

  3. Equipment – snorkel gear including vests, two person kayak with vests, floatation noodles

Marauder Sailing  Charters offers half day/full day sunset, private and custom charters from Esperanza to Sun Bay, Pata Prieta or Playulea for a guided snorkel tour.  The Marauder, a 34’ vintage sloop, has been updated with modern conveniences for your comfort.

  1. Food – gourmet lunch (featured in March 2015 issue of Elle Magazine)

  2. Beverage – all day open bar

  3. Equipment – all snorkel gear, AED

Sea Vieques offers two daily charters on the Winds of Freedom, 8:30 am to 12:30 pm and 12:30 pm to 4:30 pm, and sunset charters, 5 pm to 7 pm, from the fisherman’s pier across from the ferry dock in Isabella Segunda.  Trips to Puerto Diablo and Culebra can also be booked.  The daily trips on this 30’ Freedom sloop will take you to the amazing open water reef of Cayo Blanco, with an in-depth explanation of the abundant sea life and how to protect our precious reefs.

  1. Food – peach mango salsa, pita chips, spinach dip, granola bars and fresh fruit

  2. Beverage – open bar with specialty drinks – Pina Coladas, Pain Killers, Chichaítos and more

  3. Equipment – all snorkel gear

Ababor Sailing offers private half day or 2 hour sailing charters or a sailing class for up to four people from the fishermen’s dock on Rompeolas. These charters sail the calm leeward side of the pier on the Enterprise, a seventeen foot sloop. Half day charters will sail to Punta Arenas for snorkeling or kayaking if requested. Trips depart at 8:30 AM or 10:00 AM. Sailing rentals are available.

  1. Food- snacks

  2. Beverages- water, soda, juice

  3. Equipment- all snorkel gear, kayak

Littleboat Sailing is a fast paced romp around Ensenada Honda on Hobie Catamarans.  These guided snorkeling tours can be booked for the morning or afternoon to Lemon Reef or the mangrove forest.  Littleboat will customize your charter if you schedule ahead.

  1. Food – snacks

  2. Beverages – water

  3. Equipment – complete snorkel gear

Vieques Classic Charters lets you hop on board the Shalamar, a 47’ classic wooden yawl based in Esperanza.  The Shalamar heads east or west based on wind conditions.  Breakfast, half day and sunset cruises are available, and she can accommodate specific sailing requirements.  This trip emphasizes the sailing experience.

  1. Food – breakfast or lunch provided. Sunset – champagne and appetizers

  2. Beverages – open bar all day – alcoholic and nonalcoholic

  3. Equipment – all snorkel gear, sunscreen and towels

East Island Excursions, based out of Fajardo, features the 62’ East Wind Sailing Catamaran. This ship has a capacity of 80 guests for large wedding parties or reunions of 60 or more.  They will pick up passengers at 10 am at Mosquito Pier, Rampeolos.  Sail to Punta Arenas for snorkeling, swimming and beachcombing then return at 3:30 pm.

  1. Food – lunch buffet – fresh fruit, deli meats, cheeses, vegetarian pasta and other salads

  2. Beverages – Pina Coladas, rum punch, soda, juice, ice tea and water

  3. Equipment – all snorkel gear

  4. Food and Beverage upgrades are available

Power Out

You grab the rail a little tighter, your feet react, instinctively taking a wider stance. The Captain is urging the throttles forward to cruising speed and you feel your pulse quicken. With eyes fixated on an ever changing shore line morphing from majestic rock cliffs to glistening white sand beaches, you feel alert, in tune with what surrounds you. Yes, you are a powerboat enthusiast. Let’s get you out there.

Vieques Powercat: welcome aboard the Powercats, two luxury power catamarans, the Wildcat of 47 feet or the Wildcat Too of 51 feet, that depart from Esperanza.  These upscale cruises leave the dock at 10 am and can be booked for 4 or 6 hours.  Three hour sunset cruises and overnight trips with a Captain and an onboard chef are also available.

  1. Food – gourmet lunch; Sunset – hors d’oeuvres; Overnight – gourmet meals

  2. Beverages – beer, wine, rum punch, juice, soft drinks and water

  3. Equipment – all snorkel gear, paddleboard and kayak

Fin Time Adventures: the Fintastic, a 38’ custom sport-fisherman, offers both fishing and snorkeling or combination charters.  From Esperanza, fishing and combination charters depart at 10 am.  Snorkeling charters leave at 10 am and 1 pm.  Fin Time will also charter to Culebra from Mosquito Pier at 8:30 am, or customize to your desire.

  1. Food – snacks and sandwiches

  2. Beverages – soda, juices and water

  3. Equipment – all snorkel gear, all fishing gear

sail / power

For larger groups of up to 12 passengers, Vieques Powercat and Vieques Classic Charters offer a unique combination charter experience, sail out, power back.

The Captains and crews who charter on the waters of Vieques are as experienced and professional as you will find anywhere. Their attention to detail and emphasis on customer service guarantees a safe and memorable experience.  All Captains hold valid up to date USCG licenses, are insured and give safety instructions before departing.

Take a turn at the helm, snorkel the fabulous coral reefs filled with the dazzling colors and shapes of the abundant sea life, feel the bend of a rod, the spray on your face, and the child within reappears by spending a day “On The Water”.

Sailing / Charters

Caribbean Lady     787-930-5610 / 5611

Fin Time Adventures         787-981-4109

LittleBoat Sailing                 787.366.5202

Marauder Sailing                787-435-4858

Sea Vieques                        787-435-0256

Vieques Classic Charter   787-467-3447

Vieques Island Powercat  787-980-9978

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