14 days in Caribbean Itinerary

14 days in Caribbean Itinerary

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Route & dates

14 days in Caribbean Itinerary

Start: Toronto, Canada
Fly:  7 h 30 min
1
Philipsburg, St. Maarten-St. Martin
— 2 nights
Fly:  3 h
2
Isla de Vieques, Puerto Rico
— 4 nights
Drive + Fly:  2 h 15 min
3
Culebra, Puerto Rico
— 3 nights
Fly:  30 min
4
San Juan, Puerto Rico
— 3 nights
Fly:  3 h 30 min
5
Providenciales, Turks and Caicos
— 1 night
Fly:  4 h 45 min
End: Toronto, Canada

2
nights
Philipsburg, St. Maarten-St. Martin

Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
On the 3rd (Sun), don't miss a visit to Frontstreet. Get ready for a full day of sightseeing on the next day: stop by Le Grande Marche, then kick back and relax at Maho Beach, and then get some thrills on the water with a speed boat tour.

Take the guesswork out of planning a Philipsburg vacation by using our trip itinerary maker.

Toronto, Canada to Philipsburg is an approximately 7.5-hour flight. You can also do a combination of shuttle and flight. The time zone difference when traveling from Toronto to Philipsburg is 1 hour. Traveling from Toronto in May, expect nights in Philipsburg to be warmer, around 29°C, while days are somewhat warmer, around 34°C. Wrap up your sightseeing on the 5th (Tue) to allow time to travel to Isla de Vieques.

Things to do in Philipsburg

Outdoors Beaches Parks

Side Trips

Maho Beach, Le Grande Marche, Orient Bay Beach, Dawn Beach
Highlights from your plan
Speed Boats Tours
Maho Beach ©
Maho Beach
Dawn Beach ©
Dawn Beach

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.
Isla de Vieques is known for nature, beaches, and wildlife. Your plan includes some of its best attractions: contemplate the waterfront views at Sun Bay Beach, take a tour by water with Boat Tours & Water Sports, enjoy the sand and surf at Caracas Beach, and stroll through La Chiva.

To see where to stay, reviews, traveler tips, and other tourist information, read Isla de Vieques trip planning site.

Getting from Philipsburg to Isla de Vieques by flight takes about 3 hours. In May, plan for daily highs up to 34°C, and evening lows to 28°C. Wrap up your sightseeing on the 9th (Sat) early enough to travel to Culebra.

Things to do in Isla de Vieques

Outdoors Parks Beaches
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
La Chiva ©
La Chiva
Vieques National Wildlife Refuge ©
Vieques National Wildlife Refuge

3
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.
Culebra is known for beaches, wildlife, and nature. Your plan includes some of its best attractions: enjoy the sand and surf at Flamenco Beach, get a new perspective on things with Boat Tours & Water Sports, stroll through Playa Punta Soldado Beach, and head off the coast to Culebrita Island.

For traveler tips, photos, and tourist information, read our Culebra road trip app.

You can do a combination of car and flight from Isla de Vieques to Culebra in 2.5 hours. Alternatively, you can ride a ferry. In May in Culebra, expect temperatures between 36°C during the day and 29°C at night. Wrap up your sightseeing on the 12th (Tue) to allow time to fly to San Juan.

Things to do in Culebra

Outdoors Parks Beaches
Highlights from your plan
Culebrita Island ©
Culebrita Island
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach

3
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Explore San Juan's surroundings by going to El Yunque Rain Forest (in El Yunque National Forest) and Museo del Tabaco Caguas (in Caguas). There's lots more to do: appreciate the extensive heritage of Old San Juan, appreciate the history behind Ballaja Sculpture, stop by Pure Soul Living, and steep yourself in history at Sitio Histórico de San Juan.

To find traveler tips, reviews, more things to do, and tourist information, read San Juan online road trip planner.

San Juan is just a stone's throw from Culebra. In May, daytime highs in San Juan are 36°C, while nighttime lows are 28°C. Wrap up your sightseeing on the 15th (Fri) early enough to travel to Providenciales.

Things to do in San Juan

Historic Sites Tours Wildlife

Side Trips

Casa Bacardi Puerto Rico, El Yunque Rain Forest, Museo del Tabaco Caguas
Highlights from your plan
El Yunque Rain Forest ©
El Yunque Rain Forest
Old San Juan ©
Old San Juan
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan

1
night
Providenciales, Turks and Caicos

Providenciales ©
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
On the 16th (Sat), stop by Atelys, view the masterpieces at Orion Creations handmade in T.C.I located at Serene By Mel, then enjoy the sand and surf at Grace Bay Beach, and finally play a few rounds at Provo Golf Club.

For more things to do, traveler tips, maps, and tourist information, refer to the Providenciales trip builder app.

You can fly from San Juan to Providenciales in 3.5 hours. Another option is to do a combination of car and flight. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. Expect a daytime high around 35°C in May, and nighttime lows around 29°C. Cap off your sightseeing on the 16th (Sat) early enough to travel back home.

Things to do in Providenciales

Outdoors Golf Beaches
Highlights from your plan
Grace Bay Beach ©
Grace Bay Beach
Provo Golf Club ©
Provo Golf Club
Atelys ©
Atelys

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