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Top US Virgin Islands Sailing Trips

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US Virgin Islands Tours

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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
SPECIAL - All Inclusive Day Sail

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful …More

5.0 (1)

SPECIAL - All Inclusive Day Sail

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful...

5 hours
5.0 (1)
from
$1,550
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 Day Charter Classic Sailboat

To maximize your day and our destination options in the National Park, we offer flexible timing allowing for an easy transfer away from the busy …More

5.0 (70)

Private Day Charter Classic Sailboat

To maximize your day and our destination options in the National Park, we offer flexible timing allowing for an easy transfer away from the busy...

4 to 5 hours Hotel pickup offered Free Cancellation
5.0 (70)
from
$1,395
Learn to Sail - Sailing Lessons All Inclusive

With 20 years of experience sailing here in the US Virgin Islands we have found that our guests value the smaller venue for purists sailing. …More

5.0 (4)

Learn to Sail - Sailing Lessons All Inclusive

With 20 years of experience sailing here in the US Virgin Islands we have found that our guests value the smaller venue for purists sailing....

5 hours
5.0 (4)
from
$1,395
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
SPECIAL - (Up to 4 Passengers) All Inclusive Day Sail

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful …More

5.0 (3)

SPECIAL - (Up to 4 Passengers) All Inclusive Day Sail

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful...

5 hours
5.0 (3)
from
$1,347
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
Turtles Guaranteed! Fuel Price Included. Smooth, Comfortable Ride

We would love to host you all and show you a wonderful day on the water! This itinerary is set to maximize witnessing the beauty …More

5.0 (1)

Turtles Guaranteed! Fuel Price Included. Smooth, Comfortable Ride

We would love to host you all and show you a wonderful day on the water! This itinerary is set to maximize witnessing the beauty...

5 hours Free Cancellation
5.0 (1)
from
$1,300
National Park & Surrounding Cays Sunset Sail

Sail the beautiful and calm protected waters of the Virgin Islands National Park aboard your private and all inclusive sailboat. Full Day, all inclusive, private …More

Cruz Bay, US Virgin Islands
5.0 (13)

National Park & Surrounding Cays Sunset Sail

Sail the beautiful and calm protected waters of the Virgin Islands National Park aboard your private and all inclusive sailboat. Full Day, all inclusive, private...

2 to 3 hours Free Cancellation
5.0 (13)
from
$1,000
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

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