60 days in Caribbean Itinerary

60 days in Caribbean Itinerary

Created using Inspirock Caribbean tour itinerary maker

Plan created by another user.Make it yours

Route & dates

1
Philipsburg, St. Maarten-St. Martin
— 8 nights
2
Culebra, Puerto Rico
— 6 nights
3
San Juan, Puerto Rico
— 9 nights
4
Isla de Vieques, Puerto Rico
— 10 nights
5
Punta Cana, Dominican Republic
— 8 nights
6
Providenciales, Turks and Caicos
— 5 nights
7
George Town, Cayman Islands
— 5 nights
8
Havana, Cuba
— 7 nights

8
nights
Philipsburg, St. Maarten-St. Martin

Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Philipsburg is known for shopping, beaches, and wildlife. Your plan includes some of its best attractions: stroll through Maho Beach, kick back and relax at Orient Bay Beach, make a trip to Frontstreet, and try your luck at Casino Royale.

Plan my Philipsburg trip by asking Inpirock to come up with tips and suggestions.

Amsterdam, The Netherlands to Philipsburg is an approximately 12-hour flight. The time zone changes from Central European Standard Time (CET) to Atlantic Standard Time (AST), which is usually a -5 hour difference. Traveling from Amsterdam in June, expect nights in Philipsburg to be warmer, around °C, while days are somewhat warmer, around °C. Wrap up your sightseeing on the 9th (Tue) to allow time to travel to Culebra.

Things to do in Philipsburg

Parks Outdoors Beaches

Side Trips

Saint-Martin, Simpson Bay, Maho, Sint Maarten, Cupecoy Bay Beach
Find places to stay Jun 1 — 9:
Highlights from your plan
Speed Boats Tours
Maho Beach ©
Maho Beach
Mullet Bay Beach ©
Mullet Bay Beach

6
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, enjoy the sea views from Culebrita Lighthouse, tour the pleasant surroundings at Playa Punta Soldado Beach, and head off the coast to Culebrita Island.

Start your trip to Culebra by creating a personalized itinerary on Inspirock.

Traveling by flight from Philipsburg to Culebra takes 5.5 hours. Expect a daytime high around °C in June, and nighttime lows around °C. Wrap up your sightseeing on the 15th (Mon) early enough to travel to San Juan.

Things to do in Culebra

Parks Outdoors Beaches
Find places to stay Jun 9 — 15:
Highlights from your plan
Culebrita Island ©
Culebrita Island
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach

9
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 Salto de Collores (in Juana Diaz), Museo del Tabaco Caguas (in Caguas) and El Yunque Rain Forest (in El Yunque National Forest). There's much more to do: take an in-depth tour of Museo de Arte de Ponce, get to know the fascinating history of Old San Juan, enjoy the sand and surf at Carolina Beach, and skim along the rocks with a canyoning and rapelling tour.

To find more things to do and other tourist information, read our San Juan itinerary planner.

Traveling by flight from Culebra to San Juan takes 2 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and shuttle. June in San Juan sees daily highs of °C and lows of °C at night. Wrap up your sightseeing on the 24th (Wed) to allow time to travel to Isla de Vieques.

Things to do in San Juan

Outdoors Parks Beaches

Side Trips

Carolina, Ponce, Luquillo, Salto de Collores, Museo del Tabaco Caguas
Find places to stay Jun 15 — 24:
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Museo de Arte de Ponce ©
Museo de Arte de Ponce

10
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: tour the pleasant surroundings at Sun Bay Beach, kick back and relax at La Chiva, deepen your appreciation for local ecosystems through Eco Tours, and take in the waterfront at Malecon.

For photos and tourist information, go to the Isla de Vieques itinerary maker.

Fly from San Juan to Isla de Vieques in 2 hours. Alternatively, you can do a combination of car and ferry; or do a combination of shuttle and ferry. In June, plan for daily highs up to °C, and evening lows to °C. Cap off your sightseeing on the 4th (Sat) early enough to travel to Punta Cana.

Things to do in Isla de Vieques

Parks Outdoors Beaches
Find places to stay Jun 24 — Jul 4:
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
Vieques National Wildlife Refuge ©
Vieques National Wildlife Refuge
Media Luna Beach ©
Media Luna Beach

8
nights
Punta Cana, Dominican Republic

Punta Cana ©
In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Explore the numerous day-trip ideas around Punta Cana: La Romana (Altos de Chavon & Teeth Of The Dog) and Conquista Park (in Bayahibe). Spend a day of island exploring on the 6th (Mon) at Saona Island. And it doesn't end there: tour the pleasant surroundings at Bavaro Beach, get a new perspective on things with Boat Tours & Water Sports, kick back and relax at Playa La Vacama, and play a few rounds at La Cana Golf Course.

To find reviews, more things to do, traveler tips, and other tourist information, read our Punta Cana sightseeing planning tool.

Traveling by flight from Isla de Vieques to Punta Cana takes 5 hours. Alternatively, you can do a combination of ferry, taxi, and bus; or do a combination of ferry and shuttle. In July, daily temperatures in Punta Cana can reach °C, while at night they dip to °C. Finish your sightseeing early on the 12th (Sun) so you can travel to Providenciales.

Things to do in Punta Cana

Outdoors Parks Golf

Side Trips

La Romana, Conquista Park, Saona Island
Find places to stay Jul 4 — 12:
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Saona Island ©
Saona Island
Safaris

5
nights
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.
Providenciales is known for beaches, wildlife, and nature. Your plan includes some of its best attractions: enjoy the sand and surf at Grace Bay Beach, contemplate the long history of Cheshire Hall Plantation, tour the pleasant surroundings at Long Bay Beach, and see the vivid underwater world at Smith's Reef.

To see photos, reviews, and tourist information, refer to the Providenciales route planner.

Traveling by flight from Punta Cana to Providenciales takes 6.5 hours. The time zone difference when traveling from Punta Cana to Providenciales is minus 1 hour. July in Providenciales sees daily highs of °C and lows of °C at night. Wrap up your sightseeing on the 17th (Fri) to allow time to travel to George Town.

Things to do in Providenciales

Outdoors Parks Beaches

Side Trip

Smith's Reef
Find places to stay Jul 12 — 17:
Highlights from your plan
Grace Bay Beach ©
Grace Bay Beach
Little Water Cay ©
Little Water Cay
Smith's Reef
Smith's Reef

5
nights
George Town, Cayman Islands

George Town ©
George Town is a city situated on Grand Cayman island of the Cayman Islands. George Town is known for wildlife, adventure, and breweries & distilleries. Your plan includes some of its best attractions: tour the pleasant surroundings at Stingray City Grand Cayman, Head underground at Cayman Crystal Caves, explore the activities along Devil's Grotto, and enjoy the sand and surf at Rum Point.

For reviews, traveler tips, ratings, and more tourist information, read George Town trip planner.

Fly from Providenciales to George Town in 8.5 hours. In July, plan for daily highs up to °C, and evening lows to °C. Cap off your sightseeing on the 22nd (Wed) early enough to travel to Havana.

Things to do in George Town

Parks Wildlife Outdoors

Side Trip

Grand Cayman
Find places to stay Jul 17 — 22:
Highlights from your plan
Cayman Spirits Co. Distillery ©
Cayman Spirits Co. Distillery
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Mastic Trail ©
Mastic Trail

7
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
When in Havana, make a side trip to see Playa Paraiso in Cayo Largo, approximately Cayo Largo away. And it doesn't end there: don't miss a visit to Malecón of Havana, appreciate the extensive heritage of Old Havana, contemplate the long history of Old Square (Plaza Vieja), and take an in-depth tour of Museum of the Revolution (Museo de la Revolucion).

To find maps, other places to visit, where to stay, and more tourist information, refer to the Havana day trip planning site.

Traveling by flight from George Town to Havana takes 4 hours. Traveling from George Town in July, expect a bit cooler with lows of °C in Havana. Wrap up your sightseeing on the 29th (Wed) to allow time to travel back home.

Things to do in Havana

Historic Sites Tours Outdoors

Side Trip

Playa Paraiso
Find places to stay Jul 22 — 29:
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Plaza de la Catedral ©
Plaza de la Catedral

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