18 days in Caribbean Itinerary

18 days in Caribbean Itinerary

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Route & dates

18 days in Caribbean Itinerary

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
Fly + taxi:  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
Fly:  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.
You'll get in some beach time at Zoni Beach and Brava Beach. Get outdoors at Flamenco Beach and Melones Beach. The adventure continues: stop by Zinkowski Art Studio, enjoy the sand and surf at Carlos Rosario Beach, visit a coastal fixture at Culebrita Lighthouse, and head off the coast to Culebrita Island.

To find photos, more things to do, other places to visit, and more tourist information, use the Culebra trip tool .

Dallas, USA to Culebra is an approximately 9-hour flight. You can also do a combination of flight, shuttle, and ferry; or do a combination of car and flight. The time zone difference moving from Central Standard Time to Atlantic Standard Time is 2 hours. Traveling from Dallas in April, expect Culebra to be somewhat warmer, temps between 85°F and 76°F. Finish your sightseeing early on the 23rd (Tue) to allow enough time 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.
Get in touch with nature at El Yunque Rain Forest and Condado Beach. Satisfy your inner culture vulture at Old San Juan and San Juan National Historic Site. When in San Juan, make a side trip to see The Innovation in Fajardo, approximately 1h 15 min away. It doesn't end there: stop by The Butterfly People.

For where to stay, photos, and tourist information, read our San Juan driving holiday planning tool .

San Juan is just a stone's throw from Culebra. April in San Juan sees daily highs of 87°F and lows of 75°F at night. Finish your sightseeing early on the 26th (Fri) so you can travel to St. Jean.

Things to do in San Juan

Parks Wildlife Outdoors

Side Trips

El Yunque Rain Forest, The Innovation
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
San Juan National Historic Site ©
San Juan National Historic Site

2
nights
St. Jean, St. Barthelemy

St. Jean ©
Kick off your visit on the 27th (Sat): contemplate the long history of Corossol, kick back and relax at Colombier Beach, and then kick back and relax at St. Jean Beach. Get ready for a full day of sightseeing on the 28th (Sun): enjoy the sand and surf at Anse des Flamands, then tour the pleasant surroundings at Anse de Grande Saline, then tour the pleasant surroundings at Grand Cul de Sac Beach, and finally look for gifts at Sea Spice.

For reviews, photos, other places to visit, and other tourist information, go to the St. Jean trip planner .

Getting from San Juan to St. Jean by flight takes about 4.5 hours. Other options: do a combination of flight and ferry. Wrap up your sightseeing on the 28th (Sun) to allow time to ride a ferry to Sandy Ground.

Things to do in St. Jean

Beaches Outdoors Parks

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 ©
On the 29th (Mon), contemplate the waterfront views at Maundays Bay, then enjoy the sand and surf at Rendezvous Bay Beach, and then stroll through Sandy Ground. On the next day, enjoy the sand and surf at Meads Bay, then tour the pleasant surroundings at Shoal Bay, and then tour the pleasant surroundings at Little Bay.

For reviews, more things to do, maps, and more tourist information, refer to the Sandy Ground online trip maker .

Traveling by ferry from St. Jean to Sandy Ground takes an hour. Alternatively, you can do a combination of flight and ferry. In April in Sandy Ground, expect temperatures between 85°F during the day and 75°F at night. Cap off your sightseeing on the 30th (Tue) early enough to travel to Isla de Vieques.

Things to do in Sandy Ground

Parks Beaches Outdoors

Side Trips

Meads Bay, Shoal Bay, Little Bay, Maundays 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.
Give yourself a bit of retail therapy at Siddhia Hutchinson Fine Art Gallery and Isla Vida. Relax by the water at Sun Bay and La Chiva. And it doesn't end there: take in the exciting artwork at Gallery Galleon, kick back and relax at La Plata Beach, tour the pleasant surroundings at Navio Beach, and look for all kinds of wild species at Vieques National Wildlife Refuge.

To see other places to visit, reviews, maps, and more tourist information, read Isla de Vieques online tour planner .

Getting from Sandy Ground to Isla de Vieques by flight takes about 3.5 hours. Other options: do a combination of ferry and flight; or do a combination of flight and ferry. In April, plan for daily highs up to 85°F, and evening lows to 75°F. Finish your sightseeing early on the 4th (Sat) so you can 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 ©
Sun Bay
La Chiva ©
La Chiva
Media Luna Beach ©
Media Luna Beach

2
nights
George Town, Cayman Islands

George Town ©
George Town is a city situated on Grand Cayman island of the Cayman Islands. Satisfy your inner culture vulture at Cayman Islands National Museum and Davinoff's Concrete Sculpture Garden. Get in touch with nature at Cayman Turtle Centre: Island Wildlife Encounter and Mastic Trail. And it doesn't end there: see some colorful creatures with a scuba or snorkeling tour, enjoy the sand and surf at Rum Point, step into the grandiose world of Pedro St. James National Historic Site, and brush up on your knowledge of spirits at Cayman Spirits Co. Distillery.

To see photos, traveler tips, more things to do, and more tourist information, refer to the George Town online tour itinerary planner .

Traveling by flight from Isla de Vieques to George Town takes 8 hours. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. In May, daytime highs in George Town are 87°F, while nighttime lows are 77°F. Finish your sightseeing early on the 7th (Tue) to allow enough 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
Stingray City ©
Stingray City
Scuba & Snorkeling

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