Caribbean Tours & Trips
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The best Caribbean tour packages
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MelissaCaribbean travel expert at TourRadar
Sailing through the marvellous Caribbean
2 Reviews by TourRadar travelers“It's the best way to see the remote islands of St Lucia/St Vincent and learn the basics of sailing.”
Jessie, traveled in March 2024
A 15-day Caribbean sailing voyage from Martinique takes you to pristine locations like Tobago Cays and Mustique. Snorkel in coral reefs, wander through Port Elisabeth's colorful wooden houses, and visit the Old Hegg Turtle Sanctuary in Bequia. Suitable for ages 20+, with nights anchored in sheltered bays and dining at local restaurants.
Duration 15 days Destinations Martinique, Saint Lucia, Saint Vincent and the Grenadines, Grenada Age Range 20 to 40 year olds Operated in English, German Operator sailwithus From
- US$1,917+$518 local payments
The luxury yacht Emerald Azzurra departs St. Thomas for pristine Caribbean destinations like White Bay Beach on Jost Van Dyke and Cruz Bay's bustling waterfront. This 8-day voyage includes stops at Culebra's marine-rich reefs, Gustavia's French-influenced shores, and concludes in historic St. John's, Antigua, with all-inclusive dining and signature cocktails.
Duration 8 days Destinations Virgin Islands, U.S., Puerto Rico, Virgin Island, British, Antigua and Barbuda Age Range up to 90 year olds Operator Emerald Cruises From $8,390
51% Off- US$4,115You save $4,275
The luxurious Emerald Azzurra yacht takes you through 8 stunning Caribbean islands in 15 days. Visit Pink Sandy Beach in Barbuda, tour the historic Fort Napoleon in Les Saintes, and snorkel in Culebra's vibrant coral reefs. Savor French-Caribbean fusion in Gustavia and see The Baths' granite formations in Virgin Gorda.
Duration 15 days Destinations Antigua and Barbuda, Guadeloupe, Virgin Island, British, Virgin Islands, U.S., Puerto Rico Age Range up to 90 year olds Operator Emerald Cruises From $16,780
28% Off- US$12,110You save $4,670
Norwegian Dawn sails from Tampa for a 13-day singles adventure through pristine Caribbean ports. Swim in Saona Island's crystal waters in Dominican Republic, meet stingrays at Grand Cayman's North Sound, and visit Aruba's California lighthouse. The trip features guided excursions to Blue Hole falls in Ocho Rios and Hato Caves in Curacao.
Duration 13 days Destinations USA, Dominican Republic, Virgin Island, British, Aruba, Jamaica, Cayman Islands Age Range 35 to 70 year olds Operator Best Single Travel From
28% Off- US$2,989
A 6-day private Caribbean escape through Jamaica awaits. Scale the iconic 900-foot Dunn's River Falls, swim with horses at Negril Beach, and spot endemic wildlife in Trelawny Parish's caves. Relax at charming Country Beach Cottages in Negril with dedicated English-speaking guides.
Duration 6 days Destinations Montego Bay, Ocho Rios, Negril Age Range 1 to 99 year olds Operator Agate Travel From
28% Off- US$4,029
What people love about Caribbean Tours
- Sailing through the marvellous Caribbean
I loved this tour. It’s not a luxury cruise, you live aboard the boat and cook together. It’s managed by a German company, being non-German speaking I had no issues, the skipper and other crew members could speak English well. This is the best way to see the remote islands of St Lucia/St Vincent and learn the basics of sailing.
- Explore Jamaica
Great to have the trip on the Explore list. Adding a day or two to the trip would have allowed us to see a bit more of some places
Travel Caribbean your way
For sailors wanting to discover hidden Caribbean spots, our top pick is a 14-day journey starting in Martinique that takes you past St. Vincent's volcanic shores and into Bequia's vibrant Port Elisabeth. The protected lagoon at Tobago Cays is where our travelers love to drop anchor and snorkel around the coral reefs. There's also an 8-day route through the British Virgin Islands, Puerto Rico and also St. Barths where you can swim right off the yacht and play with marine equipment. What makes these trips special is the mix of actual sailing lessons, cooking together and getting to less-visited islands. Our customers tell us these voyages work best if you want hands-on sailing rather than a luxury cruise experience.
See all Sailing toursThe Caribbean comes alive through our private guided tours that go beyond the usual tourist spots. Jamaica's customized experiences take you right into island life - you'll climb the cascading waters at Dunn's River Falls, paddle down the winding Rio Grande and jump into the clear blue pools at Blue Hole. Over in Puerto Rico, our customers particularly enjoy combining hikes through El Yunque's lush rainforest with evening kayak trips in Fajardo Bay where the water glows with bioluminescence. The Dominican Republic tours head off-grid to special places like the Larimar mines, the only spot on Earth where you can find this rare blue stone. These explorer routes blend physical activities with real cultural moments - one day you're learning coffee-making techniques at Blue Mountain and the next you're sipping rum at Pelican Bar, a quirky spot built right out in the Caribbean Sea.
See all Explorer toursSelect from our extensive range of 61 fully guided tours to enjoy a worry-free experience through Caribbean with our expert guides leading the way.
See all Fully Guided toursFind the right partially guided tour for you in Caribbean. There are 26 trips to choose from, that range from 4 days in length, up to 90 days. The month with the most departures is April, making it the most popular time to visit Caribbean.
See all Partially Guided tours
Top operators in Caribbean
Based on the provided feedback, your best options are really between these two tour companies, and they each excel in different areas. Across Caribbean Excursions does a solid job with their week-long Bahamas program - our travelers consistently mention how well-organized everything is and they appreciate getting a proper mix of activities while still connecting with local culture. Explore's Jamaica tour has built up quite a following too, especially for travelers who want to dig deeper into island life. The local guides make a big difference here - they take you through working coffee plantations and rum distilleries instead of just hitting tourist spots. What's particularly good about both companies is they don't just rush you from place to place. They've clearly put thought into the pacing and timing of activities, markets, beach time and cultural visits. Our customers regularly tell us they appreciate having enough time to properly experience each stop rather than just ticking boxes. I should note that while we don't have extensive review data yet, the feedback we do have from travelers who've taken these tours in the past year has been consistently positive, especially about the cultural elements and activity mix.
- 4.5 (7 Caribbean reviews)
"Everything went very smoothly. Questions were answered quickly in advance. The sailing trip was fantastically beautiful and exactly what I had imagined. The route was determined by the crew and everyone was able to contribute their wishes. For me, it was a successful trip that was a lot of fun and relaxing. All in all, a clear recommendation!
- Tours
- 1 Caribbean tours
- Age range
- 20 to 40 years old
- Adventure type
- Sailing
- Response time
- 13h
- Response rate
- 100%
- Average price
- $184
- 4.5 (26 Caribbean reviews)
- Tours
- 23 Caribbean tours
- Age range
- 12 to 90 years old
- Adventure type
- Sailing
- Response time
- 17h
- Response rate
- 81%
- Average price
- $2945
- 5.0 (307 Caribbean reviews)
- Tours
- 6 Caribbean tours
- Age range
- 1 to 99 years old
- Adventure type
- Explorer
- Response time
- 2h
- Response rate
- 100%
- Average price
- $1113
Caribbean tours for every type of group
Who are you traveling with?
Group
80 tours in CaribbeanThe group tours really tap into Caribbean culture and give you time to properly explore each place. In Kingston, you get three full days to soak up the music scene and visit coffee farms up in the Blue Mountains. Our travelers tell us they love how varied each day is - one morning you're learning about Rastafarian life in a local community, then by afternoon you're floating down the Rio Grande on a bamboo raft. There's a good mix of beach time and cultural visits; you might start at Frenchman's Cove then head to historic Port Royal later. The schedule includes group meals with local dishes and also leaves room for exploring on your own, especially around Negril's Seven Mile Beach and Montego Bay's lively strip.
Small Group
22 tours in CaribbeanSmall group sailing through the Caribbean creates an intimate way to discover hidden corners of these islands. The 14-day voyages from Martinique let you actively participate in sailing, while exploring quiet spots like Petit Tabac, Mayreau's pristine beaches and also hidden coves. Our travelers especially connect with cooking together on deck and picking up sailing basics from experienced skippers. The Jamaica route has become quite popular, where groups immerse themselves in island culture - from climbing Dunn's River Falls to touring Blue Mountain coffee estates, wandering through Trench Town's vibrant music scene. These tours blend physical activity with cultural connections naturally; you might spend a morning rafting the Rio Grande then visit a Maroon village in the afternoon. The flotilla-style Caribbean sailing works well for both new and experienced sailors, with time for snorkeling in Tobago Cays' coral reefs and exploring spots like Port Elisabeth where colorful wooden houses line the streets. Our customers often tell us how the small group size helps them connect with fellow travelers while keeping the flexibility to stay longer in places that spark their interest.
Private / Personalized
24 tours in CaribbeanPrivate tours let you set the pace while keeping those genuine local connections. In Jamaica, your guide can read the room - if you're loving Blue Hole's waterfalls, you stay longer, or if you want extra time perfecting your coffee at Craighton Plantation, that's fine too. Over in the Dominican Republic, these tours often head to quieter spots like Black River for crocodile watching or mountain villages where you'll learn proper jerk cooking. Our guests really value how the day can shift - maybe an active morning climbing Dunn's River Falls followed by a quiet afternoon on a hidden beach. Special requests are no problem, whether that's more photo stops along Bamboo Avenue or timing things just right to catch those cliff divers at Rick's Café.
Top Caribbean travel itineraries to fit your plans
Ten days gives you space to understand Jamaica's real character. Starting in Kingston, our guests love experiencing both the polished uptown areas and raw energy of Trench Town's reggae culture. After exploring Blue Mountain coffee estates, you'll head to Port Antonio for Rio Grande bamboo rafting. The journey continues with time on Negril's seven-mile beach and finishes in Treasure Beach - perfect for crocodile spotting boat safaris or Jamaican cooking classes. As one of our customers put it: "the gentle pace was exactly what I needed after leaving work behind."
TourRadar recommends visiting:
Saint Barthélemy, Anguilla
See all tours
Two-week sailing trips reveal how different each Caribbean island really is. Starting from Barbados or Bridgetown, you'll cruise through the Grenadines and stop at Tobago Cays for turtle snorkeling in impossibly clear water. The route takes in French-influenced spots like Îles des Saintes and Saint Barthélemy, plus historical sites including Antigua's Nelson's Dockyard. You'll explore natural features like The Baths at Virgin Gorda and also lesser-known gems such as the wave-formed natural jacuzzi at Jost Van Dyke's Bubbly Pool.
TourRadar recommends visiting:
Bridgetown, Soufriere, Iles des Saintes, Falmouth Harbour, Barbados, Gustavia, Marigot, Anguilla, Virgin Gorda Island, Norman Island, Jost van Dyke, Anegada
Demographics
The sailing tours around St. Lucia and St. Vincent tend to attract solo travelers who want to meet new people. You can get involved with the actual sailing if you're interested, or just relax and enjoy the group dinners and beach stops. Our 14-day routes take you to quiet spots like Petit Tabac, Mayreau and other hidden coves where the small groups make it natural to connect while exploring local beaches and bars.
For couples, we've developed private tours through Jamaica's quieter areas where you control the pace between coffee plantations and empty beaches. Puerto Rico offers some really nice romantic elements - evening walks in Old San Juan paired with kayaking in glowing bioluminescent waters. In the Dominican Republic, you can enjoy private beach picnics and guided walks through Los Haitises National Park. Most couples like how we mix active mornings in caves or at waterfalls with laid-back afternoons at small boutique hotels.
Our yacht tours through the Virgin Islands and Puerto Rico really click with young adults looking for social activities. Mornings might find you snorkeling Norman Island's caves, afternoons testing out water sports off the yacht and evenings joining beach BBQs with live music. The night kayaking in Vieques' bio bay is always popular, as are the beach clubs in St. Barths. We keep the schedule flexible so you can join group activities or explore on your own.
Our cultural tours in Jamaica work particularly well for senior travelers - we use comfortable hotels as bases while exploring the island's heritage sites. You'll visit historic Devon House, learn about coffee growing in the Blue Mountains and take it all in at a comfortable pace. In the Dominican Republic, we run easy-going tours through Santo Domingo's colonial zone with regular breaks and good transport. The guides adjust things based on mobility levels while making sure everyone gets to experience the real Caribbean.
Our family tours in Curaçao mix learning with pure fun - kids particularly love spotting fish while snorkeling at the Blue Room cave's crystal waters. Parents tell us they appreciate how we pace things, with plenty of beach time at Klein Curaçao and walks through Willemstad where the Dutch-style buildings catch children's attention. Jamaica works really well for families too; the Dunn's River Falls climbs and gentle river tubing are always highlights. Over in the Dominican Republic, we've picked family-friendly resorts with lots of organized activities and included guided trips to places like Harrison's Cave where electric trams take you through impressive caverns.
Solo Travelers78 tours All tours for Solo Travelers- Couples48 tours
- Seniors (50+)35 tours All tours for Seniors
Best time to visit Caribbean
- Spring 2025
Jamaica really comes into its own in spring. The Kingston tours start at the Bob Marley Museum, then head up to local Blue Mountain coffee plantations for afternoon tastings. Port Antonio's spring activities mix bamboo river rafting with dips in the Blue Lagoon. Puerto Rico offers some great combinations - you can hike El Yunque rainforest trails and then paddle through bioluminescent waters at night. Our Barbados visitors in April start at Harrison's Cave, continue to Hunte's Gardens and usually end up joining the turtle-watching snorkel sessions along the west coast.
- 52 tours
- popular 54 tours
- 49 tours
- Summer 2025
Summer in the Dominican Republic and Puerto Rico brings out some unique experiences. Around Puerto Plata, you can join eco-projects building bottle homes and learning about local environmental work. The afternoons cool off with swims at Dudu Ecological Park's freshwater lagoon or snorkeling near Sosúa's corals. Puerto Rico's summer schedule makes good use of the long days - you'll walk through Old San Juan as the sun sets and catch early ferries to Culebra's beaches. The water activities really pick up with speedboat rides to distant cays and night kayaking in glowing waters.
- 47 tours
- popular 49 tours
- 43 tours
- Fall / Autumn 2025
Fall means better value and fewer crowds at Jamaica's top spots. You get more space to explore Blue Mountains coffee farms and extra time watching sunsets at Treasure Beach. Our travelers tell us they love the relaxed pace through Port Antonio, with plenty of swimming time at Frenchman's Cove and also the Blue Lagoon. The weather works perfectly for Dunn's River Falls climbs and Rose Hall Great House visits. The days usually wrap up at Rick's Cafe - you can watch the cliff divers with a sunset backdrop and then enjoy some live reggae.
- 44 tours
- popular 47 tours
- 39 tours
- Winter 2025 / 2026
The Caribbean winter sailing scene opens up some fantastic routes through quiet bays. You can join multi-day trips around St. Vincent and the Grenadines, where nights are spent cooking together on deck and anchoring in peaceful spots. Over in Barbuda, the yacht tours take you past pink-sand beaches and let you watch frigate birds at their UNESCO sanctuary. Our customers really enjoy stopping in Les Saintes for the French-Caribbean fusion food, especially the local coconut cake near Fort Napoleon. The Norman Island circuit includes snorkeling at old pirate caves, and there's plenty of time at hidden beaches. The British Virgin Islands yacht tours finish perfectly with beach BBQs and live music at White Bay Beach on Jost Van Dyke.
- February 2025 popular 47 tours
- 39 tours
- 24 tours
Contact our Caribbean travel experts
Steffanie
Expert in Caribbean at TourRadar
Steffanie is one of our seasoned Caribbean Travel Experts. Reach out to us to get all your questions about Caribbean tours answered!
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