14 days in Caribbean Itinerary

14 days in Caribbean Itinerary

Created using Inspirock trip maker

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1
Isla de Vieques, Puerto Rico
— 4 nights
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2
San Juan, Puerto Rico
— 4 nights
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3
Culebra, Puerto Rico
— 2 nights
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4
Charlotte Amalie, U.S. Virgin Islands
— 3 nights
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Isla de Vieques, Puerto Rico

— 4 nights

Isla Nena

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.
Isla de Vieques is known for beaches, nature, and wildlife. Your plan includes some of its best attractions: enjoy the sand and surf at Balneario Sun Bay, tour the pleasant surroundings at Caracas Beach, take in the waterfront at Malecon, and head off the coast to Vieques Island.

To see traveler tips, photos, maps, and more tourist information, read our Isla de Vieques trip itinerary planning site.

St. Croix, U.S. Virgin Islands to Isla de Vieques is an approximately 3.5-hour flight. In December in Isla de Vieques, expect temperatures between 34°C during the day and 28°C at night. Cap off your sightseeing on the 3rd (Sun) early enough to travel to San Juan.

Things to do in Isla de Vieques

Outdoors · Parks · Beaches · Tours
Find places to stay Dec 30 — Jan 3:

San Juan, Puerto Rico

— 4 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
Explore San Juan's surroundings by going to El Yunque National Forest (El Portal Tropical Forest Center & El Yunque Rain Forest). There's much more to do: appreciate the extensive heritage of Sitio Histórico de San Juan, pause for some photo ops at Paseo de los Presidentes, get interesting insight from Tours, and kick back and relax at Condado Beach.

Make your San Juan itinerary with Inspirock to find out what to see and where to go.

Fly from Isla de Vieques to San Juan in 2 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and shuttle. In January, daily temperatures in San Juan can reach 34°C, while at night they dip to 26°C. Wrap up your sightseeing on the 7th (Thu) early enough to travel to Culebra.

Things to do in San Juan

Outdoors · Tours · Parks · Historic Sites

Side Trip

Find places to stay Jan 3 — 7:

Culebra, Puerto Rico

— 2 nights

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
On the 8th (Fri), kick back and relax at Playa Punta Soldado Beach and then kick back and relax at Flamenco Beach. On the 9th (Sat), you'll have a packed day of sightseeing: head off the coast to Culebrita and then get interesting insight from Tours.

To find where to stay, other places to visit, maps, and other tourist information, refer to the Culebra tour itinerary builder app.

Traveling by flight from San Juan to Culebra takes 2 hours. Alternatively, you can do a combination of car and ferry; or do a combination of shuttle and ferry. In January, daily temperatures in Culebra can reach 34°C, while at night they dip to 26°C. Finish your sightseeing early on the 9th (Sat) so you can travel to Charlotte Amalie.

Things to do in Culebra

Outdoors · Parks · Beaches · Tours
Find places to stay Jan 7 — 9:

Charlotte Amalie, U.S. Virgin Islands

— 3 nights

Duty-free Capital of the World

One of the most visited cruise ship destinations in the Caribbean, the town of Charlotte Amalie is known around the world for its duty-free jewelry, perfume, and liquor shops.
Kick off your visit on the 10th (Sun): look for gifts at Diamonds International, make a trip to Main Street, and then kick back and relax at Magens Bay. On the next day, enjoy the sand and surf at Coki Point Beach, then get to know the resident critters at Coral World Ocean Park, and then get a new perspective on things with Boat Tours & Water Sports.

For more things to do, maps, traveler tips, and other tourist information, you can read our Charlotte Amalie road trip app.

You can fly from Culebra to Charlotte Amalie in 5 hours. In January, plan for daily highs up to 34°C, and evening lows to 26°C. Wrap up your sightseeing by early afternoon on the 12th (Tue) to allow enough time to travel back home.

Things to do in Charlotte Amalie

Outdoors · Parks · Beaches · Shopping

Side Trips

Find places to stay Jan 9 — 12:

St. Thomas travel guide

4.2
Beaches · Gift & Specialty Shops · Scuba & Snorkeling
Plan a trip to St. Thomas for a holiday full of duty-free shopping, relaxing, and sightseeing. Although the most commercialized of the U.S. Virgin Islands, St. Thomas is rich in culture and history. A popular cruise ship destination, the hilly island boasts idyllic beaches, upscale resorts, a lively nightlife, and a fine dining scene. Whether you're looking to visit churches and museums, laze on tropical beaches, or have an outdoor adventure, you won't run out of things to do on St. Thomas.