Celebrate Valentine's Day in Caribbean (Updated 2026)

Caribbean
Private Catamaran Charter on Wyuna

This is not your average boat charter—Sail Bermuda offers a luxury private sailing experience that’s entirely your own. Whether you want to snorkel offshore reefs …More

Likely to Sell Out
Likely to Sell Out

This is not your average boat charter—Sail Bermuda offers a luxury private sailing experience that’s entirely your own. Whether you want to snorkel offshore reefs...

3 hours Free Cancellation
5.0 (17)
from
$2,120
Classic Beach Break

Lunch amazing. served under a shady pavilion.We have there own private area, beautiful beach, shade loungers. Bar is there just for your group, very inexpensive..3 …More

Lunch amazing. served under a shady pavilion.We have there own private area, beautiful beach, shade loungers. Bar is there just for your group, very inexpensive..3...

4 hours Hotel pickup offered Free Cancellation
4.7 (86)
from
$51
Port Royal (UNESCO World Heritage site)and Downtown Kingston Tour

Our history tours have been enjoyed by many visitors. We offer an enriching travel experience - accompanying and guiding visitors around Port Royal, a guided …More

Our history tours have been enjoyed by many visitors. We offer an enriching travel experience - accompanying and guiding visitors around Port Royal, a guided...

6 to 7 hours Hotel pickup offered Free Cancellation
5.0 (25)
from
$110
3 Hours Private Boat Includes Snorkeling & Swim with turtles

Experience Aruba’s stunning coastline aboard a private speed boat charter. This exclusive 3 hour adventure is perfect for families, friends, and small groups looking for …More

Experience Aruba’s stunning coastline aboard a private speed boat charter. This exclusive 3 hour adventure is perfect for families, friends, and small groups looking for...

3 hours Free Cancellation
5.0 (43)
from
$900
Curaçao AquaJet Underwater Scooter Adventure

Experience Curacao's vibrant reefs with ease as our powerful Sublue scooters let you glide faster, farther, and with less effort, making it fun for all …More

Experience Curacao's vibrant reefs with ease as our powerful Sublue scooters let you glide faster, farther, and with less effort, making it fun for all...

1 hour Free Cancellation
5.0 (20)
from
$120
Bioluminescent Bay Boat Tour in La Parguera

Relax on a smooth charter through La Parguera’s Bioluminescent Bay and discover one of Puerto Rico’s most magical natural wonders. Glide across calm, glowing waters, …More

Relax on a smooth charter through La Parguera’s Bioluminescent Bay and discover one of Puerto Rico’s most magical natural wonders. Glide across calm, glowing waters,...

1 hour Free Cancellation
4.7 (60)
from
$80
Curaçao: Clear Boat Experience – Crystal Waters & Marine Life

Glide across the turquoise waters of Curaçao aboard our unique clear boat, designed to give you crystal-clear views of coral reefs, tropical fish, and even …More

Glide across the turquoise waters of Curaçao aboard our unique clear boat, designed to give you crystal-clear views of coral reefs, tropical fish, and even...

1 hour 30 minutes Free Cancellation
4.9 (42)
from
$115
Original Exuma Powerboat Adventures

Leaving the hustle-bustle of Nassau behind, take a high-powered cruise to your own private island in the Exuma chain. You'll ride a powerboat to Allens …More

Leaving the hustle-bustle of Nassau behind, take a high-powered cruise to your own private island in the Exuma chain. You'll ride a powerboat to Allens...

9 hours Hotel pickup offered Free Cancellation
4.9 (488)
from
$329
Klein Curacao Sunset Cruise with Open Bar and BBQ

Prepare to be whisked away to an uninhabited island as we set sail from the mainland of Curacao to the stunning Klein Curacao. As we …More

Prepare to be whisked away to an uninhabited island as we set sail from the mainland of Curacao to the stunning Klein Curacao. As we...

8 hours Free Cancellation
4.8 (71)
from
$165
Private Premium Whale and Dolphin Safari St Lucia

Spend the day out on the water off the coast of St Lucia on this whale and dolphin watching cruise! With 85% chance of sightings, …More

Likely to Sell Out
Likely to Sell Out

Spend the day out on the water off the coast of St Lucia on this whale and dolphin watching cruise! With 85% chance of sightings,...

4 hours Free Cancellation
4.7 (70)
from
$2,000
Beach Trip Along The West Coast Of Curacao

Sailing along Curacao’s West Coast on the biggest catamaran of Curacao is a must do attraction! The trip starts at 08:30 am. As soon as …More

Sailing along Curacao’s West Coast on the biggest catamaran of Curacao is a must do attraction! The trip starts at 08:30 am. As soon as...

8 hours Free Cancellation
4.9 (44)
from
$140
Barbados Full-day Coast to Coast Tour

This is Barbados coastal exploration that takes you through historic Bridgetown onto the affluent West Coast, through Holetown, through Speightstown, continuing onto North Point. Travel …More

This is Barbados coastal exploration that takes you through historic Bridgetown onto the affluent West Coast, through Holetown, through Speightstown, continuing onto North Point. Travel...

6 hours Hotel pickup offered Free Cancellation
4.7 (293)
from
$125
Exhilarating Dunn's River Falls Guided Tour from Ocho Rios hotels

Holiday Services is the multiple time winner of the "Best Tour Operator of the year award"for excellence in tourism. 41 years in business, Jamaican owned …More

Holiday Services is the multiple time winner of the "Best Tour Operator of the year award"for excellence in tourism. 41 years in business, Jamaican owned...

2 hours 30 minutes Hotel pickup offered Free Cancellation
4.6 (74)
from
$65
Rainforest Trek to Natural Pool - Taino Bay & Amber Cove ports

Trek through a beautiful tropical forest, crossing a suspension bridge and streams while discovering the flora, fauna and medicinal plants along the way to a …More

Trek through a beautiful tropical forest, crossing a suspension bridge and streams while discovering the flora, fauna and medicinal plants along the way to a...

240 to 270 minutes Free Cancellation
4.7 (54)
from
$79
Saona Island Excursion From Punta Cana

We're taking you to the Super-Star of off-shore islands in the Dominican Republic. Think sun, sand, booze, boats and bikinis! You can thank us later …More

We're taking you to the Super-Star of off-shore islands in the Dominican Republic. Think sun, sand, booze, boats and bikinis! You can thank us later...

8 hours Hotel pickup offered Free Cancellation
4.3 (430)
from
$82
Party Boat Cruise from Punta Cana

Embark on an unforgettable afternoon of fun and adventure with the Catamaran and Snorkeling Tour from Punta Cana! Immerse yourself in breathtaking coastal views, snorkel …More

Embark on an unforgettable afternoon of fun and adventure with the Catamaran and Snorkeling Tour from Punta Cana! Immerse yourself in breathtaking coastal views, snorkel...

3 to 4 hours Hotel pickup offered Free Cancellation
4.8 (167)
from
$89
Bluefinn242 Swim with the Turtles in Nassau Bahamas

This trip begins with a brief harbour tour with historical sights, a fifteen minute cruise over to green cay or what’s better known as turtle …More

This trip begins with a brief harbour tour with historical sights, a fifteen minute cruise over to green cay or what’s better known as turtle...

2 hours Free Cancellation
4.8 (300)
from
$135
Antigua VIP Tours - Semi-Private Gold Tour

Experience Antigua in privacy and comfort in 5 hours on our Semi-Private tour and enjoy beach views, get a glimpse into our history and culture, …More

Experience Antigua in privacy and comfort in 5 hours on our Semi-Private tour and enjoy beach views, get a glimpse into our history and culture,...

5 hours Hotel pickup offered Free Cancellation
4.9 (155)
from
$135
Luxury Catamaran Cruise: Sip, Sail, Snorkel, and Swim with Pigs!

Dive into a world of difference with Tropical Breeze as we redefine the classic Bahamian cruise experience. Here's what sets us apart as the ultimate …More

Dive into a world of difference with Tropical Breeze as we redefine the classic Bahamian cruise experience. Here's what sets us apart as the ultimate...

6 hours Free Cancellation
5.0 (89)
from
$179
Flavors of St Lucia Culinary Experience

Our Flavors of St. Lucia Tour is a wonderful culinary and educational experience! Suit up in your Apron and Chef hat (provided) and let’s get …More

Our Flavors of St. Lucia Tour is a wonderful culinary and educational experience! Suit up in your Apron and Chef hat (provided) and let’s get...

3 hours Hotel pickup offered Free Cancellation
4.8 (43)
from
$130
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