St Thomas Sailing Trips

34 Results
Private Full Day Sail/ Snorkel Experience USVI (Sapphire Marina, STT pick up)

This is a private personal sailing experience for up to six guest. Avoid the crowds and choose how you want to spend the best day …More

Likely to Sell Out
Likely to Sell Out

This is a private personal sailing experience for up to six guest. Avoid the crowds and choose how you want to spend the best day...

7 hours Free Cancellation
5.0 (18)
from
$1,975
Private Full Day Sail in Virgin Islands National Park

On a private full day sail with Max Charters you will have the boat to yourself! Your captain and mate will take you to some …More

Likely to Sell Out
Likely to Sell Out

On a private full day sail with Max Charters you will have the boat to yourself! Your captain and mate will take you to some...

6 hours Free Cancellation
5.0 (16)
from
$1,650
Private Sunset Sailor's Delight from Sapphire Marina

This is an private intimate trip for up to six guest. Avoid the crowds and enjoy a 2 hour leisurely sail with your loved ones …More

Likely to Sell Out
Likely to Sell Out

This is an private intimate trip for up to six guest. Avoid the crowds and enjoy a 2 hour leisurely sail with your loved ones...

2 hours Free Cancellation
5.0 (15)
from
$795
Amazing Half Day Private Boat Charter on Luxury Sailing Catamaran

Swim and snorkel beautiful reefs. See the amazing beaches and Islands while catching some sun on the bean bags on top of the trampolines. You …More

Likely to Sell Out
Likely to Sell Out

Swim and snorkel beautiful reefs. See the amazing beaches and Islands while catching some sun on the bean bags on top of the trampolines. You...

4 hours 30 minutes Free Cancellation
5.0 (12)
from
$250
Discover the Best of St. John - Snorkel, Beach & Shopping!

Experience the best of two tropical islands! Sail to the island escape of St. John from St. Thomas aboard the beautiful Lady Lynsey. After snorkeling …More

Cruz Bay, US Virgin Islands

Experience the best of two tropical islands! Sail to the island escape of St. John from St. Thomas aboard the beautiful Lady Lynsey. After snorkeling...

5 hours Hotel pickup offered Free Cancellation
4.9 (7)
from
$129
Private Sunset Sail, Open Bar, 12 Guests, Amazing Island Views

You will set sail aboard one of the largest daysail yachts in the Virgin Islands. At 55 feet the Blue Dream is well equipped to …More

Likely to Sell Out
Likely to Sell Out

You will set sail aboard one of the largest daysail yachts in the Virgin Islands. At 55 feet the Blue Dream is well equipped to...

2 hours Free Cancellation
5.0 (6)
from
$1,345
I Like Turtles Private Sailing and Snorkeling from Sapphire

Come sail on a beautiful classic monohaul sailboat. You're guaranteed to enjoy your day sailing and snorkeling with amazing green sea turtles here in the …More

Likely to Sell Out
Likely to Sell Out

Come sail on a beautiful classic monohaul sailboat. You're guaranteed to enjoy your day sailing and snorkeling with amazing green sea turtles here in the...

3 hours Free Cancellation
5.0 (3)
from
$799
Private Luxury Veuve Clicquot Sunset Champagne Yacht Charter

Your private group up to 12 individuals will enjoy a Luxury Sunset and Champagne cruise about our luxury 50' Voyage catamaran. We head out early …More

Likely to Sell Out
Likely to Sell Out

Your private group up to 12 individuals will enjoy a Luxury Sunset and Champagne cruise about our luxury 50' Voyage catamaran. We head out early...

2 hours Free Cancellation
5.0 (2)
from
$1,495
St Thomas Pizza Pi Snorkel Sail From Frenchman's Reef

Start the day with a sail to an offshore cay for premier snorkeling. In addition to fruit, salads, and cookies, our main lunch will be …More

Start the day with a sail to an offshore cay for premier snorkeling. In addition to fruit, salads, and cookies, our main lunch will be...

5 hours Free Cancellation
5.0 (2)
from
$139
Days End Sunset Sail with Open Bar from Frenchman's Reef

Step aboard our luxury sailing catamaran for a fun and relaxing sunset sail departing from Frenchman’s Reef. Take in a magnificent Caribbean sunset while under …More

Step aboard our luxury sailing catamaran for a fun and relaxing sunset sail departing from Frenchman’s Reef. Take in a magnificent Caribbean sunset while under...

1 hour 30 minutes Free Cancellation
4.6 (78)
from
$89
St. Thomas Dinner Sail to St. John with Open Bar - Ritz-Carlton

Step aboard our luxury 53 foot catamaran for an evening escape to the island of St. John. This popular sail departs directly from The Ritz-Carlton …More

Step aboard our luxury 53 foot catamaran for an evening escape to the island of St. John. This popular sail departs directly from The Ritz-Carlton...

5 hours Free Cancellation
4.7 (56)
from
$149
Days End Sunset Sail with Open Bar from St. Thomas Ritz-Carlton

Enjoy a relaxing and romantic sail in the calm waters of Pillsbury Sound with views of the beautiful beaches on the north shore of St. …More

Enjoy a relaxing and romantic sail in the calm waters of Pillsbury Sound with views of the beautiful beaches on the north shore of St....

1 hour 30 minutes Free Cancellation
4.7 (50)
from
$129
St. Thomas Dinner Sail to Lovango with Open Bar

Step aboard our luxury 65 foot catamaran Lady Lynsey II for an evening escape to the private island of Lovango Cay for dinner under the …More

Step aboard our luxury 65 foot catamaran Lady Lynsey II for an evening escape to the private island of Lovango Cay for dinner under the...

4 hours Free Cancellation
4.6 (43)
from
$129

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