18 days in Caribbean Itinerary

18 days in Caribbean Itinerary

Created using Inspirock Caribbean route maker

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Route & dates

Start: Dallas, United States
Fly:  9 h
1
Culebra, Puerto Rico
— 2 nights
Fly:  30 min
2
San Juan, Puerto Rico
— 3 nights
Fly:  4 h 30 min
3
St. Jean, St. Barthelemy
— 2 nights
+2
Ferry + Drive + Fly:  1 h
4
Sandy Ground, Anguilla
— 2 nights
Fly:  3 h 15 min
5
Isla de Vieques, Puerto Rico
— 4 nights
Fly:  7 h 45 min
6
George Town, Cayman Islands
— 2 nights
+2
Fly + Foot + Tram:  5 h
End: Dallas, United States

2
nights
Culebra, Puerto Rico

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Get outdoors at Flamenco Beach and Melones Beach. Visit Zoni Beach and Brava Beach for some beach relaxation. There's still lots to do: look for gifts at Zinkowski Art Studio, head off the coast to Culebrita Island, enjoy the sand and surf at Tamarindo Beach, and stroll through Playa Punta Soldado Beach.

To find traveler tips, other places to visit, where to stay, and other tourist information, go to the Culebra route planner.

Dallas, USA to Culebra is an approximately 10.5- hour flight. You can also do a combination of tram and flight; or do a combination of tram, flight, shuttle, and ferry. The time zone changes from Central Standard Time (CST) to Atlantic Standard Time (AST), which is usually a 2 hour difference. Expect a bit warmer temperatures when traveling from Dallas in April; daily highs in Culebra reach 85°F and lows reach 76°F. Wrap up your sightseeing on the 23rd (Tue) early enough to fly to San Juan.

Things to do in Culebra

Parks Beaches Outdoors
Find places to stay Apr 21 — 23:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach
Tamarindo Beach ©
Tamarindo Beach

3
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Visiting El Yunque Rain Forest and Condado Beach will get you outdoors. Get a sense of the local culture at Old San Juan and Sitio Histórico de San Juan. When in San Juan, make a side trip to see The Innovation in Fajardo, approximately Fajardo away. Next up on the itinerary: stop by The Butterfly People.

To find other places to visit, ratings, more things to do, and other tourist information, use the San Juan trip planner.

San Juan is just a short distance from Culebra. In April, daily temperatures in San Juan can reach 87°F, while at night they dip to 75°F. Wrap up your sightseeing on the 26th (Fri) to allow time to travel to St. Jean.

Things to do in San Juan

Wildlife Parks Outdoors

Side Trips

The Innovation, El Yunque Rain Forest
Find places to stay Apr 23 — 26:
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan

2
nights
St. Jean, St. Barthelemy

St. Jean ©
Kick off your visit on the 27th (Sat): steep yourself in history at Corossol, stroll through Colombier Beach, and then tour the pleasant surroundings at St. Jean Beach. Get ready for a full day of sightseeing on the 28th (Sun): kick back and relax at Anse des Flamands, then stroll through Anse de Grande Saline, then stroll through Grand Cul de Sac Beach, and finally shop like a local with Sea Spice.

To find more things to do, maps, ratings, and tourist information, you can read our St. Jean online tour itinerary planner.

You can fly from San Juan to St. Jean in 3.5 hours. Another option is to do a combination of flight and ferry. Wrap up your sightseeing on the 28th (Sun) to allow time to travel to Sandy Ground.

Things to do in St. Jean

Beaches Parks Outdoors

Side Trips

St. Barthelemy, Grand Cul de Sac Beach
Find places to stay Apr 26 — 28:
Highlights from your plan
St. Jean Beach ©
St. Jean Beach
Colombier Beach ©
Colombier Beach
Grand Cul de Sac Beach ©
Grand Cul de Sac Beach

2
nights
Sandy Ground, Anguilla

Sandy Ground ©
Sandy Ground is a village and one of the fourteen Districts of Anguilla, and its main port. Start off your visit on the 29th (Mon): contemplate the waterfront views at Maundays Bay, stroll through Rendezvous Bay Beach, and then tour the pleasant surroundings at Sandy Ground. Keep things going the next day: enjoy the sand and surf at Meads Bay, then kick back and relax at Shoal Bay, and then enjoy the sand and surf at Little Bay.

To see photos, where to stay, other places to visit, and other tourist information, you can read our Sandy Ground road trip planning site.

You can do a combination of ferry and flight from St. Jean to Sandy Ground in 2 hours. Other options are to do a combination of flight and ferry; or ride a ferry. In April, daytime highs in Sandy Ground are 85°F, while nighttime lows are 75°F. Finish your sightseeing early on the 30th (Tue) so you can travel to Isla de Vieques.

Things to do in Sandy Ground

Parks Beaches Outdoors

Side Trips

Shoal Bay, Little Bay, Maundays Bay, Meads Bay
Find places to stay Apr 28 — 30:
Highlights from your plan
Shoal Bay ©
Shoal Bay
Rendezvous Bay Beach ©
Rendezvous Bay Beach
Meads Bay ©
Meads Bay

4
nights
Isla de Vieques, Puerto Rico

Isla de Vieques ©
For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
Escape the urban bustle at Sun Bay Beach and La Chiva. Get a sense of the local culture at Siddhia Hutchinson Fine Art Gallery and Puerto Ferro Lighthouse. And it doesn't end there: take in the exciting artwork at Serenity Point Yoga & Visionary Arts Space, tour the pleasant surroundings at Green Beach, enjoy the sand and surf at La Plata Beach, and look for all kinds of wild species at Wildlife Areas.

For other places to visit, traveler tips, more things to do, and other tourist information, refer to the Isla de Vieques trip planner.

You can fly from Sandy Ground to Isla de Vieques in 3 hours. Another option is to do a combination of ferry and flight. In April, daily temperatures in Isla de Vieques can reach 85°F, while at night they dip to 75°F. Wrap up your sightseeing on the 4th (Sat) to allow time to travel to George Town.

Things to do in Isla de Vieques

Outdoors Parks Beaches
Find places to stay Apr 30 — May 4:
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
Media Luna Beach ©
Media Luna Beach
La Chiva ©
La Chiva

2
nights
George Town, Cayman Islands

George Town ©
George Town is a city situated on Grand Cayman island of the Cayman Islands. Visit Seven Mile Beach and Rum Point for some beach relaxation. Escape the urban bustle at Stingray City Grand Cayman and Cayman Turtle Centre: Island Wildlife Encounter. Step out of George Town with an excursion to Davinoff's Concrete Sculpture Garden in North Side--about 48 minutes away. There's still lots to do: take a memorable tour with Tours, sample the fine beverages at Cayman Spirits Co. Distillery, admire the natural beauty at Queen Elizabeth II Botanic Park, and explore the galleries of Cayman Islands National Museum.

For photos, traveler tips, where to stay, and other tourist information, read George Town sightseeing planning site.

You can fly from Isla de Vieques to George Town in 7.5 hours. The time zone difference when traveling from Isla de Vieques to George Town is minus 1 hour. In May, plan for daily highs up to 87°F, and evening lows to 77°F. Wrap up your sightseeing on the 7th (Tue) to allow time to travel back home.

Things to do in George Town

Parks Wildlife Outdoors

Side Trips

Grand Cayman, Seven Mile Beach, Cayman Turtle Centre: Island Wildlife Encounter, Davinoff's Concrete Sculpture Garden
Find places to stay May 4 — 7:
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Scuba & Snorkeling
Stingray City Grand Cayman ©
Stingray City Grand Cayman

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