Top Caribbean Sailing Trips

Q: Which Caribbean Sailing Trips have Instant Confirmation?

Caribbean Sailing Trips with Instant Confirmation include: Exclusive Hip Hop Punta Cana Party Boat with Open Bar *Only Adult 7 Hour Private Catamaran Sail, Snorkel and Beach BBQ Grace Bay, Providenciales 2 days 1 night by private catamaran from St Martin to St Barth 2.5hr Private Catamaran Cruise with Snorkeling, Bar, Food St Martin Gd-Case: Private day in all inclusive catamaran View all Tours with Instant Confirmation →

Q: Got any more Caribbean trip ideas?

We sure do. Check out our curated lists of hand-picked Caribbean Tours. Top 10 Caribbean 2026 Senior-friendly tours Caribbean The best tours and activities for culture lovers in Caribbean Top Day Trips from Caribbean Things to do in Caribbean this summer View all Caribbean Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Caribbean?

Based on our sales data over the past year, the most popular styles of tours and activities in Caribbean are: Caribbean Luxury & Special Occasions Caribbean Luxury Tours Caribbean Tours & Sightseeing Caribbean Shore Excursions Caribbean Port Transfers View all tour styles in Caribbean →

Party Boat Cruise & Open Bar with Snorkeling in Punta Cana

Our animation team and captain are highly trained for this type of events with a lot of experience in this type of adventures, fun professionals …More

Punta Cana, Dominican Republic

3.0 (1)

Party Boat Cruise & Open Bar with Snorkeling in Punta Cana

Our animation team and captain are highly trained for this type of events with a lot of experience in this type of adventures, fun professionals...

4 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$69

Iconic Aruba Sail and Snorkel Experience

Experience the joy of sailing along Aruba’s stunning beaches on a spacious catamaran & snorkeling at the marine sanctuary, Catalina bay, and the famous Antilla shipwreck. …More

4.8 (510)

Iconic Aruba Sail and Snorkel Experience

Experience the joy of sailing along Aruba’s stunning beaches on a spacious catamaran & snorkeling at the marine sanctuary, Catalina bay, and the famous Antilla shipwreck....

2 hours 30 minutes Free Cancellation

4.8 (510)

from
$67

No1Sxm Sunset Sail Experience in St Maarten

Are you ready to go Sailing? TRUE sailing on board of No1Sxm Trimaran: stable, smooth, comfortable. The 2 hour Sailing Experience is pure bliss, with …More

4.9 (304)

No1Sxm Sunset Sail Experience in St Maarten

Are you ready to go Sailing? TRUE sailing on board of No1Sxm Trimaran: stable, smooth, comfortable. The 2 hour Sailing Experience is pure bliss, with...

2 hours Free Cancellation

4.9 (304)

from
$67

Banana Adventure Catamaran Shipwreck Snorkel and Turtle Swim

*Professional and friendly crew* *Snorkeling equipment and safety briefing* *Delicious snacks and refreshments* *Access to the rope swing and diving platform* *Comfortable seating and shaded …More

4.8 (233)

Banana Adventure Catamaran Shipwreck Snorkel and Turtle Swim

*Professional and friendly crew* *Snorkeling equipment and safety briefing* *Delicious snacks and refreshments* *Access to the rope swing and diving platform* *Comfortable seating and shaded...

3 hours Hotel pickup offered Free Cancellation

4.8 (233)

from
$65

Your 4-hours glass bottom boat and reef adventure from Punta Cana begins by meeting your friendly local guide at your hotel in Punta Cana and …More

Punta Cana, Dominican Republic

4.4 (14)

Glass Bottom Boat in Punta Cana

Your 4-hours glass bottom boat and reef adventure from Punta Cana begins by meeting your friendly local guide at your hotel in Punta Cana and...

4 hours Hotel pickup offered Free Cancellation

4.4 (14)

from
$65

We offer a fun-filled tour on a catamaran with a slide riding by the coast and National drinks open bar included, snacks, music on board, …More

5.0 (6)

Party Boat Punta Cana all included

We offer a fun-filled tour on a catamaran with a slide riding by the coast and National drinks open bar included, snacks, music on board,...

4 hours Free Cancellation

5.0 (6)

from
$65

Hip Hop Party boat booze cruise w Open Bar (adults only)

Enjoy a fun party atmosphere in our 3 hour all you can drink hip hop party boat cruise. A quick stop for snorkeling, drinks in …More

5.0 (4)

Hip Hop Party boat booze cruise w Open Bar (adults only)

Enjoy a fun party atmosphere in our 3 hour all you can drink hip hop party boat cruise. A quick stop for snorkeling, drinks in...

3 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$65

Two Hours of Sailing and Relaxation in the Bay of Saintes

In an intimate setting (max 7 people), come and discover the Saintes archipelago by sail! I'll take you to Terre de Bas to observe the …More

4.9 (11)

Two Hours of Sailing and Relaxation in the Bay of Saintes

In an intimate setting (max 7 people), come and discover the Saintes archipelago by sail! I'll take you to Terre de Bas to observe the...

2 hours Free Cancellation

4.9 (11)

from
$63

Arusun Catamaran Sail with Snorkeling in Aruba

Arusun is no ordinary tour boat. She is a 60-foot Formula II Ocean Racing Catamaran designed by Rod McAlpine-Downie and built in 1984–1985 for serious …More

4.9 (2,583)

Arusun Catamaran Sail with Snorkeling in Aruba

Arusun is no ordinary tour boat. She is a 60-foot Formula II Ocean Racing Catamaran designed by Rod McAlpine-Downie and built in 1984–1985 for serious...

2 hours 30 minutes Free Cancellation

4.9 (2,583)

from
$63

Small Group: Snorkeling Cruise Adventure around the Punta Cana Coast

SINGLES, COUPLES & GROUPS can all explore the beautiful coast of Punta Cana on this safe route. Embark on a party in one of the …More

Punta Cana, Dominican Republic

4.9 (38)

Small Group: Snorkeling Cruise Adventure around the Punta Cana Coast

SINGLES, COUPLES & GROUPS can all explore the beautiful coast of Punta Cana on this safe route. Embark on a party in one of the...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (38)

from
$60

Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran

Welcome aboard the “DOLPHIN”! Join us for an breathtaking sunset sail we’ll make sure it will be the highlight of your vacation! Our professional staff …More

4.7 (763)

Aruba Sunset Sail Cruise Aboard The Dolphin Catamaran

Welcome aboard the “DOLPHIN”! Join us for an breathtaking sunset sail we’ll make sure it will be the highlight of your vacation! Our professional staff...

2 hours Free Cancellation

4.7 (763)

from
$59

Punta Cana Catamaran Party Cruise with Unlimited Drinks

Spend a different time aboard this boat animated by a staff that will make you enjoy a pleasant time. A great way to spend a …More

Punta Cana, Dominican Republic

4.3 (206)

Punta Cana Catamaran Party Cruise with Unlimited Drinks

Spend a different time aboard this boat animated by a staff that will make you enjoy a pleasant time. A great way to spend a...

4 hours Hotel pickup offered Free Cancellation

4.3 (206)

from
$59

Punta Cana Party Boat Cruise: Snorkeling, Open Bar & Natural Pool

Turn a day in Punta Cana into a Caribbean party on the water aboard a lively catamaran cruise along the beautiful Bavaro coastline. This experience …More

4.6 (15)

Punta Cana Party Boat Cruise: Snorkeling, Open Bar & Natural Pool

Turn a day in Punta Cana into a Caribbean party on the water aboard a lively catamaran cruise along the beautiful Bavaro coastline. This experience...

3 hours 30 minutes Hotel pickup offered Free Cancellation

4.6 (15)

from
$59

Punta Cana Scuba Doo: Underwater Scooter Adventure

Discover a different side of Punta Cana with a Scuba Doo underwater scooter experience that lets you explore beneath the Caribbean Sea without traditional scuba …More

Punta Cana, Dominican Republic

3.8 (13)

Punta Cana Scuba Doo: Underwater Scooter Adventure

Discover a different side of Punta Cana with a Scuba Doo underwater scooter experience that lets you explore beneath the Caribbean Sea without traditional scuba...

3 hours 30 minutes Hotel pickup offered Free Cancellation

3.8 (13)

from
$59

Full Day Excursion to Isla Saona from Punta Cana

Isla Saona is the perfect excursion for those tourists who are looking for a healthy and fun getaway. You will also have the opportunity to …More

Punta Cana, Dominican Republic

4.0 (15)

Full Day Excursion to Isla Saona from Punta Cana

Isla Saona is the perfect excursion for those tourists who are looking for a healthy and fun getaway. You will also have the opportunity to...

10 hours Hotel pickup offered Free Cancellation

4.0 (15)

from
$58

This is Punta Cana like you’ve never imagined. Parasailing is a thrilling activity that’ll have you whooping over the Caribbean. After pick-up, head to Corales …More

Punta Cana, Dominican Republic

4.8 (25)

Parasailing in Bavaro

This is Punta Cana like you’ve never imagined. Parasailing is a thrilling activity that’ll have you whooping over the Caribbean. After pick-up, head to Corales...

2 hours Hotel pickup offered Free Cancellation

4.8 (25)

from
$57

Experience the romance of a Caribbean sunset on a Champagne cruise in St Maarten. While you sail along the coast on a luxury catamaran, enjoy …More

4.7 (83)

Sunset Champagne Cruise in St. Maarten

Experience the romance of a Caribbean sunset on a Champagne cruise in St Maarten. While you sail along the coast on a luxury catamaran, enjoy...

1 hour 30 minutes Free Cancellation

4.7 (83)

from
$55

Beach Buggy Excursion in Punta Cana Bavaro

It is a short activity of only 4 hours so you will have the whole day to enjoy your hotel once finished. You can choose …More

Punta Cana, Dominican Republic

4.0 (1)

Beach Buggy Excursion in Punta Cana Bavaro

It is a short activity of only 4 hours so you will have the whole day to enjoy your hotel once finished. You can choose...

4 hours Hotel pickup offered Free Cancellation

4.0 (1)

from
$54

Punta Cana Party Booze Cruise, open bar, snorkeling Only Adult

Set Sail in Punta Cana – Bavaro Luxury, Fun & VIP Vibes All in One! Perfect for birthdays, bachelorette parties, group getaways & more. WHAT’S INCLUDED? …More

La Romana, Dominican Republic

4.8 (77)

Punta Cana Party Booze Cruise, open bar, snorkeling Only Adult

Set Sail in Punta Cana – Bavaro Luxury, Fun & VIP Vibes All in One! Perfect for birthdays, bachelorette parties, group getaways & more. WHAT’S INCLUDED?...

4 hours Hotel pickup offered Free Cancellation

4.8 (77)

from
$50

Half Day Party Boat and Snorkeling in Punta Cana

What makes our experience unique is the perfect mix of Caribbean rhythm, crystal-clear waters, and true Dominican hospitality. Our goal is always your happiness — …More

Punta Cana, Dominican Republic

4.5 (4)

Half Day Party Boat and Snorkeling in Punta Cana

What makes our experience unique is the perfect mix of Caribbean rhythm, crystal-clear waters, and true Dominican hospitality. Our goal is always your happiness —...

4 hours Hotel pickup offered Free Cancellation

4.5 (4)

from
$49