Trip type
Tropical islands & the Caribbean trips
Routes built around tropical islands & the Caribbean. Every one is day by day, with costs and timing; filter by where, who's coming and how long you have.
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Trip types: Festivals & events · Anniversaries & milestones · Cultural festivals & parades · National parks & wild places · Waterfalls & gorges · Volcanoes & geothermal wonders · Stargazing & northern lights · Camping & cabins · Wildlife watching & birding · Desert & canyon parks · Mountain & alpine parks · Coastal & island parks · Forests, rainforests, caves & wetlands · Road trip · Historic route · Route 66 · Natchez Trace Parkway · Mountain & scenic byways · Blue Ridge Parkway · National park road trip · Road trip abroad · Coastal drives · Pacific Coast Highway · Desert & canyon drives · Ferry & island road trip · Active & adventure trip · Paddling, kayaking & rafting · Snowshoeing, dog sledding & winter sports · Hiking & backpacking · Biking & rail-trails · Multi-sport adventure trip · City trip & culture · Live music & nightlife · Theme parks & family attractions · Museums: art, science & history · Film, TV & literary trip · Architecture & design · Theater & performing arts · Big cities · Smaller cities · Cities near the outdoors · Scenic train rides · Heritage & excursion railroads · Long-distance rail journeys · Car-free trip by train · Rail journeys abroad · Mountain getaways & ski · Ski trip · Snowy escapes without skiing · Summer mountain towns · Red rock & desert mountain towns · Alps, highlands & big ranges abroad · Spa, cruise & splurge trip · Wellness retreats & yoga · Spas & hot springs · Cruises, river & canal boats · Ocean cruises · Alaska Inside Passage cruise · Splurge trip · Slow, restful trip · History & culture · Lighthouses, forts & sea history · Castles & old towns · Mansions & grand estates · Ancient sites & ruins · Civil War sites · Historic small towns & covered bridges · Presidential & military history · Pilgrimages & sacred sites · Old West, ghost & mining towns · Civil rights & Black history · Colonial & Revolutionary history · Native American & Indigenous heritage · Beach vacations & islands · Snorkeling & diving · Beach towns · Island hopping · Tropical islands & the Caribbean · Mediterranean coasts & islands · Rugged coastlines · Surf towns · Food & wine trip · Markets, street food & food halls · Breweries & distilleries · Seafood & coastal eating · Fine-dining splurges · Wine country · Farm-to-table, orchards & cider · Coffee, cheese & sweet treats · Food cities (US & Canada) · Regional American food · Barbecue trails · Tex-Mex & Southwest flavors · Southern, Cajun & Creole cooking · Eating your way abroad · Japanese food · Italian food · Mexican food · French food · Spanish & Portuguese food · Southeast Asian food · Korean food · Central European food · Irish & British food · Bucket-list trip · Machu Picchu & the Inca Trail · Camino de Santiago · Iceland Ring Road · By departure city · From New York City · From Los Angeles · From Chicago · From Washington, DC · From Boston · From San Francisco Bay Area · By travel time · Under 2 hours by car · 2 to 4 hours by car.

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Every guide, listed by filter
Plain links to every guide in this collection ( Tropical islands & the Caribbean), grouped the same way as the filters above. A guide appears under every group it fits.
All trips →Where
Browse by where
North America 20
United States 16
New England 1
Maine 1
Midcoast 1
Southeast 8
North Carolina 1
The Coast 1
South Carolina 1
Lowcountry & Resort Islands (Charleston, Hilton Head) 1
Georgia 2
Coastal Georgia 2
Florida 4
Northwest Florida (Panhandle) 1
Central West Florida 1
Florida Keys 2
Midwest 1
Wisconsin 1
Northeast Wisconsin (Door County) 1
Mountain West 1
Utah 1
Salt Lake & Wasatch Front 1
Alaska & Hawaii 5
Hawaii 5
Oʻahu 2
Maui 1
Kauaʻi 1
Island of Hawaiʻi 1
Canada 1
Atlantic Canada 1
Prince Edward Island 1
Charlottetown & Central 1
Caribbean 3
Puerto Rico 1
St. Maarten 1
US Virgin Islands 1
South America 1
Colombia & the Caribbean coast 1
Colombia 1
Europe 3
Southern Europe & Mediterranean 2
Spain 1
Balearic Islands 1
Greece 1
Cyclades 1
Nordics & Iceland 1
Sweden 1
Oceania 1
Australia & New Zealand 1
New Zealand 1
By place type 10
Lake towns 2
Harbor & fishing villages 2
Island towns 6
Glacier & fjord country 1
Who's going
Browse by who's going
Friends 1
Friend getaways 1
Families 13
With teens 3
With little kids (under 6) 9
With school-age kids (6–12) 5
Family trip for all ages 3
First trip abroad with kids 2
Couples 12
Honeymoons 2
Romantic city breaks 2
Beach & island escapes for two 10
Mountain & ski escapes for two 1
Adventure trip for couples 5
Food & wine getaways for two 1
Multigenerational 3
Grandparents & grandkids 1
Three generations together 2
When
Browse by when
Winter 12
December 12
January 12
February 12
Warm-weather winter escapes 12
Spring 20
March 12
April 16
May 10
Summer 10
June 10
July 6
August 6
Fall 13
September 10
October 7
November 4
Seasonal events 2
Spring break 2
Trip type
Browse by trip type
National parks & wild places 13
Volcanoes & geothermal wonders 1
Stargazing & northern lights 1
Wildlife watching & birding 8
Mountain & alpine parks 1
Coastal & island parks 3
Forests, rainforests, caves & wetlands 1
Road trip 19
Road trip abroad 2
Coastal drives 18
Ferry & island road trip 2
Active & adventure trip 6
Paddling, kayaking & rafting 4
Hiking & backpacking 1
Multi-sport adventure trip 1
City trip & culture 5
Museums: art, science & history 2
Film, TV & literary trip 1
Architecture & design 1
Big cities 1
Smaller cities 3
Cities near the outdoors 1
Mountain getaways & ski 1
Alps, highlands & big ranges abroad 1
Spa, cruise & splurge trip 1
Splurge trip 1
History & culture 10
Lighthouses, forts & sea history 6
Castles & old towns 1
Civil War sites 1
Historic small towns & covered bridges 2
Beach vacations & islands 25
- Big Island
- Bradenton
- Cartagena with Friends
- Door County
- Florida Keys
- Hilton Head
- Kauai
- Key West
- Maine Coast
- Mallorca for Two
- Maui Family Trip
- New Zealand South Island
- Oahu
- Oahu
- Outer Banks
- Panama City Beach
- Prince Edward Island
- Puerto Rico
- Salt Lake City with Tweens
- Santorini for Two
- Savannah
- St. John
- St. Maarten for Two
- St. Simons Island
- Stockholm
Snorkeling & diving 9
Beach towns 5
Island hopping 2
Tropical islands & the Caribbean 25
- Big Island
- Bradenton
- Cartagena with Friends
- Door County
- Florida Keys
- Hilton Head
- Kauai
- Key West
- Maine Coast
- Mallorca for Two
- Maui Family Trip
- New Zealand South Island
- Oahu
- Oahu
- Outer Banks
- Panama City Beach
- Prince Edward Island
- Puerto Rico
- Salt Lake City with Tweens
- Santorini for Two
- Savannah
- St. John
- St. Maarten for Two
- St. Simons Island
- Stockholm
Mediterranean coasts & islands 2
Rugged coastlines 2
Surf towns 1
Food & wine trip 10
Seafood & coastal eating 4
Wine country 1
Coffee, cheese & sweet treats 2
Food cities (US & Canada) 1
Regional American food 1
Southern, Cajun & Creole cooking 1
Eating your way abroad 1
Spanish & Portuguese food 1
Bucket-list trip 1
How long
Browse by how long
Weekend (2-3 days) 4
Long weekend (4-5 days) 14
About a week (6-8 days) 7
More like this
Beach vacations & islands · Snorkeling & diving · Beach towns · Mediterranean coasts & islands · Rugged coastlines
