St. Thomas Dinner Cruises

If dinner and a sunset cruise sounds good to you, don’t miss out on Dockside Watersports’ popular sail around St. Thomas.

Dinner Sailing Tours with Dockside Watersports

The Flying Frenchman on the sea
Waterfront Harbor

Dinner Sail

STARTS AT
ADULT

$199.00

Children (Ages 3 - 12)

$149.00

Sail on a luxury catamaran

Spectacular views and photo ops of the sunset

Locally-sourced & gourmet dinner

Full open bar

Step aboard our luxurious sailing catamaran, The Flying Frenchman, for a 2-hour sail through the historic harbor of Charlotte Amalie. Enjoy an open bar and onboard dinner while taking in a magnificent Caribbean sunset. All cuisine is locally inspired and served by our professional crew. Dinner on the water surrounded by spectacular sites is the perfect way to highlight your St. Thomas visit!
Happy women toasting
Charlotte Amalie

On-Board Dinner Sail

FROM

$139.00

Luxurious Catamaran Sunset Sail

Full Open Bar

Appetizers and Cocktails While Sailing to Dinner

This popular sail departs directly from Frenchman’s Reef and begins with cocktails and appetizers while we position for the perfect view of the sunset as we make way to Charlotte Amalie where you may dine at the restaurant of your choosing.
The Flying Frenchman on the sea
Waterfront Harbor

Dinner Sail

FROM

$199.00

Luxury Catamaran Sailing

Open Bar

Locally-Inspired Dinner On Board

Step aboard the luxurious sailing catamaran Flying Frenchman for a 2-hour dinner sail through the historic harbor of Charlotte Amalie while enjoying dinner service complimented by an open bar.
Flying Frenchman
Day’s End

Sunset Sail

FROM

$119.00

Luxury Catamaran Sailing

Open Bar

Chef’s Selection of Hors d’Oeuvres

Take in a magnificent Caribbean sunset while under sail and enjoy a chef’s selection of hors d’oeuvres and open bar. This luxurious sunset sail is perfect for couples and families alike.
A group at the entrance of Jost Van Dyke for a tour
Discover

Jost Van Dyke

FROM

$219.00

Luxury Catamaran Sailing

Open Bar

Continental style breakfast

Take in a magnificent Caribbean sunset while under sail and enjoy a chef’s selection of hors d’oeuvres and open bar. This luxurious sunset sail is perfect for couples and families alike.

Experience the Difference

Let Dockside Watersports make your trip to the U.S. Virgin Islands exceptional.

Smaller Crowds

Escape large parties of guests and enjoy beautiful locations with the help of one of our captains.

Interesting Local Tidbits

See the USVI through the eyes of a local and get a fresh take on popular locations from our friendly crew members.

Luxurious Amenities

Sit back and relax on the water with comfortable seating and top-quality crew service.

Knowledgeable Crew Members

Know that you and your party are in safe hands with our highly skilled captains.

Curated Experiences

Participate in a variety of watersports activities based on your particular interests.

Great On-The-Water Service

Receive exceptional service from our friendly crew members, who help ensure a great boating experience.

Serving St Thomas Guests for Over 30 Years

With a mission of providing exceptional experiences to thousands of people a year, Dockside Watersports maintains a fleet of over 40 state-of-the-art US Coast Guard-inspected vessels across the world. 

It is through these signature experiences, high service standards, and exemplary customer service that we create luxurious and exceptional excursions for our guests. Contact us now to get more information on how we can curate your trip of a lifetime!

A couple enjoying the delightful Charlotte Amalie Dinner Sail tour
Waiter serving drinks

Reviews

Read what our customers have to say about their on-the-water excursions with Dockside Watersports.

The crew was awesome! Professional, friendly, and fun! We had a great day on the water!
Laura S.
Great time today, highly recommend to anybody. Super crew!
Don L.
Such a memorable and wonderful experience! Outstanding, knowledgeable crew and a beautiful boat to enjoy the day. Great snorkeling spots to check out.
Sara R.
We had a great time! The sunset was amazing. The crew was great! We really enjoyed being on the water and watching the sun dip down past the horizon.
Alec L.

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