cool shore excursions®
Top activities
Top landmarks
Trip ideas
Nearby places
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by time
  • Tours by the numbers
  • Top attractions
  • St Thomas travel guides
  • St Thomas travel calendar
  • Tours in nearby places
  • Explore US Virgin Islands tours
Language $Currency
Login / Sign up
Bookings
Bookings
Wallet
$0.00
Wishlists
Wishlists
Cool Rewards Rewards
Gift cards
Profile
Help Center
Language
Log out
Start your search
Change your search
Place or activity
Select Dates

Top St Thomas Sailing Trips

34 Results
Sort by:
Price (High to Low)
Filter
Languages Clear
Time of Day Clear
23
16
8
Duration Clear
0
14
21
0
0
Price Clear
$0 $500+
Rating Clear
30
34
34
Specials Clear
32
16
0
16
0
Features Clear
1
22
29
4
32
4
Accessibility Clear
0
14
27
Families Clear
15
17
10

St Thomas Tours

Attractions

Guides

Calendar

Full Day Private Charter, Snorkel St. John (12 guests, 55’ yacht)

Explore the Virgin Islands in style and luxury aboard this beautiful 54 foot sailing yacht for an amazing full day (10am - 4pm) sailing excursion. …More

5.0 (102)

Full Day Private Charter, Snorkel St. John (12 guests, 55’ yacht)

Explore the Virgin Islands in style and luxury aboard this beautiful 54 foot sailing yacht for an amazing full day (10am - 4pm) sailing excursion....

6 hours Free Cancellation
5.0 (102)
from
$1,985
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
5.0 (18)

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...

7 hours Free Cancellation
5.0 (18)
from
$1,975
St. Thomas & St. John Private Luxury Full-Day Sail (12 guest max)

If you’re looking for an unforgettable day at sea, book a private boat charter with Sweet Pea Charters. Our luxury 40 by 25 foot catamaran …More

Likely to Sell Out
Likely to Sell Out
5.0 (113)

St. Thomas & St. John Private Luxury Full-Day Sail (12 guest max)

If you’re looking for an unforgettable day at sea, book a private boat charter with Sweet Pea Charters. Our luxury 40 by 25 foot catamaran...

6 hours 30 minutes Free Cancellation
5.0 (113)
from
$1,650
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
5.0 (16)

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...

6 hours Free Cancellation
5.0 (16)
from
$1,650
Private Day Sail & Snorkel with Virgin Islands Day Sailing, 6 guest max

A Private Sailing Experience, Just for You. There is no end to what you can see while sailing with Virgin Islands Day Sailing. Join us …More

5.0 (122)

Private Day Sail & Snorkel with Virgin Islands Day Sailing, 6 guest max

A Private Sailing Experience, Just for You. There is no end to what you can see while sailing with Virgin Islands Day Sailing. Join us...

6 hours 30 minutes Free Cancellation
5.0 (122)
from
$1,495
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
5.0 (2)

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...

2 hours Free Cancellation
5.0 (2)
from
$1,495
50' Luxury Yacht. Private Full or Half Day Catamaran Snorkel, & Beach Experience

Spend the day on your own 50' Luxury Catamaran Yacht. This price is all inclusive for the Yacht, up to 12 guests. You can select …More

5.0 (681)

50' Luxury Yacht. Private Full or Half Day Catamaran Snorkel, & Beach Experience

Spend the day on your own 50' Luxury Catamaran Yacht. This price is all inclusive for the Yacht, up to 12 guests. You can select...

4 to 7 hours Free Cancellation
5.0 (681)
from
$1,441
Private Luxury Catamaran Yacht. Full or Half Day Charter - Sail, Beach, Snorkel.

Spend the day on your own Luxury Yacht. This price is all inclusive for the Yacht, up to 12 people. You can select a half …More

4.9 (423)

Private Luxury Catamaran Yacht. Full or Half Day Charter - Sail, Beach, Snorkel.

Spend the day on your own Luxury Yacht. This price is all inclusive for the Yacht, up to 12 people. You can select a half...

7 hours Free Cancellation
4.9 (423)
from
$1,356
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
5.0 (6)

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...

2 hours Free Cancellation
5.0 (6)
from
$1,345
Simply Sailing Private Sail from Sapphire Marina

This is the ideal trip for the true sailor's out there. Enjoy a private 3 hour adventure of straight sailing aboard our beautiful "Robert Perry" …More

Likely to Sell Out
Likely to Sell Out
5.0 (19)

Simply Sailing Private Sail from Sapphire Marina

This is the ideal trip for the true sailor's out there. Enjoy a private 3 hour adventure of straight sailing aboard our beautiful "Robert Perry"...

3 hours Free Cancellation
5.0 (19)
from
$799
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
5.0 (3)

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...

3 hours Free Cancellation
5.0 (3)
from
$799
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
5.0 (15)

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...

2 hours Free Cancellation
5.0 (15)
from
$795
Luxury Private Sunset Cruise for up to 6 guests

An Unforgettable Sailing Experience, Just for You. There is no end to what you can see while sailing with Virgin Islands Day Sailing. Join us …More

Likely to Sell Out
Likely to Sell Out
5.0 (38)

Luxury Private Sunset Cruise for up to 6 guests

An Unforgettable Sailing Experience, Just for You. There is no end to what you can see while sailing with Virgin Islands Day Sailing. Join us...

2 hours Free Cancellation
5.0 (38)
from
$695
Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)

The Virgin Islands are the sailing capital of the world!! Sail with us from St. Thomas to the exotic island of Jost Van Dyke. This …More

5.0 (189)

Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)

The Virgin Islands are the sailing capital of the world!! Sail with us from St. Thomas to the exotic island of Jost Van Dyke. This...

8 hours
5.0 (189)
from
$375
St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast - Ritz-Carlton

This one of a kind excursion to Jost Van Dyke allows passengers to spend the most time on the island out of all other group …More

4.9 (50)

St. Thomas Jost Van Dyke & Soggy Dollar Snorkel Sail w/ Breakfast - Ritz-Carlton

This one of a kind excursion to Jost Van Dyke allows passengers to spend the most time on the island out of all other group...

8 hours Free Cancellation
4.9 (50)
from
$309
Full Day Sail with Max Charters

A day with Max Charters is a unique way to experience the Virgin Islands. We carry fewer passengers than most charter companies in order to …More

Likely to Sell Out
Likely to Sell Out
5.0 (136)

Full Day Sail with Max Charters

A day with Max Charters is a unique way to experience the Virgin Islands. We carry fewer passengers than most charter companies in order to...

6 hours Free Cancellation
5.0 (136)
from
$285
Full-Day Sailing Tour in Virgin Islands National Park

Set sail and explore the Virgin Islands National Park! Enjoy a day of sailing and snorkeling with lunch and drinks provided! Where to meet: We …More

Likely to Sell Out
Likely to Sell Out
4.9 (49)

Full-Day Sailing Tour in Virgin Islands National Park

Set sail and explore the Virgin Islands National Park! Enjoy a day of sailing and snorkeling with lunch and drinks provided! Where to meet: We...

6 hours Free Cancellation
4.9 (49)
from
$285
6-Hour Turtles, Pizza Pi & Sunset Sail

** This trip departs from St. Thomas Only ** Get ready for a day of sun, sea, and stories! Our crew members, who also call …More

Likely to Sell Out
Likely to Sell Out
5.0 (441)

6-Hour Turtles, Pizza Pi & Sunset Sail

** This trip departs from St. Thomas Only ** Get ready for a day of sun, sea, and stories! Our crew members, who also call...

6 hours
5.0 (441)
from
$280
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
5.0 (12)

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...

4 hours 30 minutes Free Cancellation
5.0 (12)
from
$250
St John & Surrounding Cays - Full-Day Sail/Snorkel, 6 Guests Max

An Unforgettable Sailing Experience! We offer a Semi-private and all inclusive Day trip that will be the best day of your vacation. There is no …More

5.0 (700)

St John & Surrounding Cays - Full-Day Sail/Snorkel, 6 Guests Max

An Unforgettable Sailing Experience! We offer a Semi-private and all inclusive Day trip that will be the best day of your vacation. There is no...

6 hours 30 minutes Free Cancellation
5.0 (700)
from
$245

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

Recent tour reviews
View traveler photos & reviews
Activity name

St Thomas Tours
Attractions
Guides
Calendar
View more