40 days in Caribbean Itinerary

40 days in Caribbean Itinerary

Created using Inspirock Caribbean trip builder

Plan created by another user. Make it yours

Route & dates

1
Santo Domingo, Dominican Republic
— 3 nights
2
Philipsburg, St. Maarten-St. Martin
— 5 nights
3
Isla de Vieques, Puerto Rico
— 8 nights
4
San Juan, Puerto Rico
— 6 nights
5
Culebra, Puerto Rico
— 5 nights
6
Seven Mile Beach, Cayman Islands
— 3 nights
7
Havana, Cuba
— 7 nights

3
nights
Santo Domingo, Dominican Republic

Santo Domingo ©
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Santo Domingo is known for historic sites, nature, and shopping. Your plan includes some of its best attractions: make a trip to Zona Colonial, explore the galleries of Columbus Lighthouse (Faro A Colon), take some stellar pictures from Santo Domingo Skyline, and steep yourself in history at Fortaleza Ozama.

To see other places to visit, where to stay, traveler tips, and more tourist information, use the Santo Domingo trip itinerary maker app.

Auckland, New Zealand to Santo Domingo is an approximately 26-hour combination of flight and shuttle. You can also fly. Due to the time zone difference, you'll gain 16 hours traveling from Auckland to Santo Domingo. Wrap up your sightseeing on the 11th (Wed) early enough to travel to Philipsburg.

Things to do in Santo Domingo

Historic Sites Museums Zoos & Aquariums
Find places to stay Nov 8 — 11:
Highlights from your plan
Alcazar de Colon ©
Alcazar de Colon
Zona Colonial ©
Zona Colonial
Columbus Lighthouse (Faro A Colon) ©
Columbus Lighthouse (Faro A Colon)

5
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: enjoy the sand and surf at Maho Beach, make a trip to Frontstreet, try to win big at Casino Royale, and tour the pleasant surroundings at Cupecoy Bay Beach.

For ratings, where to stay, other places to visit, and other tourist information, read our Philipsburg online trip builder.

You can fly from Santo Domingo to Philipsburg in 4.5 hours. November in Philipsburg sees daily highs of °C and lows of °C at night. Finish your sightseeing early on the 16th (Mon) so you can travel to Isla de Vieques.

Things to do in Philipsburg

Outdoors Parks Beaches

Side Trips

Simpson Bay, Sint Maarten, Saint-Martin, Maho, Orient Bay Beach
Find places to stay Nov 11 — 16:
Highlights from your plan
Speed Boats Tours
Maho Beach ©
Maho Beach
Mullet Bay Beach ©
Mullet Bay Beach

8
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: enjoy the sand and surf at La Chiva, expand your understanding of the military at Camp Garcia, stroll through Media Luna Beach, and have fun at Vieques Gun Club & Sporting Clays.

To find traveler tips, photos, more things to do, and other tourist information, use the Isla de Vieques vacation builder site.

You can fly from Philipsburg to Isla de Vieques in 5.5 hours. In November, plan for daily highs up to °C, and evening lows to °C. Finish up your sightseeing early on the 24th (Tue) so you can travel to San Juan.

Things to do in Isla de Vieques

Outdoors Parks Beaches
Find places to stay Nov 16 — 24:
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
La Chiva ©
La Chiva
Scuba & Snorkeling

6
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Explore the numerous day-trip ideas around San Juan: Museo del Tabaco Caguas (in Caguas), Ponce (Museo de Arte de Ponce & Casa Wiechers-Villaronga) and El Yunque Rain Forest (in El Yunque National Forest). Next up on the itinerary: get to know the fascinating history of Old San Juan, see the sights as you ascend with a climbing tour, take a peaceful walk through Bosque Nacional El Yunque, and contemplate the long history of Sitio Histórico de San Juan.

Plan trip to San Juan with our itinerary maker to find out where to go and what to do.

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 November, daily temperatures in San Juan can reach °C, while at night they dip to °C. Finish your sightseeing early on the 30th (Mon) to allow enough time to travel to Culebra.

Things to do in San Juan

Outdoors Parks Tours

Side Trips

Ponce, Museo del Tabaco Caguas, Bosque Nacional El Yunque, Luquillo Beach, El Yunque Rain Forest
Find places to stay Nov 24 — 30:
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

5
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: kick back and relax at Flamenco Beach, tour the pleasant surroundings at Tamarindo Beach, step off the mainland to explore Culebrita Island, and visit a coastal fixture at Culebrita Lighthouse.

To find where to stay, traveler tips, ratings, and tourist information, use the Culebra trip planner.

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 November, daily temperatures in Culebra can reach °C, while at night they dip to °C. Finish up your sightseeing early on the 5th (Sat) so you can travel to Seven Mile Beach.

Things to do in Culebra

Parks Outdoors Beaches
Find places to stay Nov 30 — Dec 5:
Highlights from your plan
Culebrita Island ©
Culebrita Island
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach

3
nights
Seven Mile Beach, Cayman Islands

Seven Mile Beach ©
Seven Mile Beach is a long crescent of coral-sand beach on the western end of Grand Cayman island. Seven Mile Beach is known for wildlife, beaches, and spas. Your plan includes some of its best attractions: tour the pleasant surroundings at Stingray City Grand Cayman, explore the striking landscape at Hell Gift Store, explore the fascinating underground world of Cayman Crystal Caves, and laugh and play at Cayman Turtle Centre: Island Wildlife Encounter.

For other places to visit, photos, maps, and other tourist information, you can read our Seven Mile Beach vacation planner.

Traveling by flight from Culebra to Seven Mile Beach takes 12 hours. You'll gain 1 hour traveling from Culebra to Seven Mile Beach due to the time zone difference. In December in Seven Mile Beach, expect temperatures between °C during the day and °C at night. Wrap up your sightseeing on the 8th (Tue) early enough to travel to Havana.

Things to do in Seven Mile Beach

Parks Wildlife Outdoors

Side Trips

Grand Cayman, Cayman Spirits Co. Distillery, Cayman Turtle Centre: Island Wildlife Encounter
Find places to stay Dec 5 — 8:
Highlights from your plan
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Seven Mile Beach ©
Seven Mile Beach

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.
Get out of town with these interesting Havana side-trips: Cayo Largo (Playa Paraiso & Sirena Beach). Next up on the itinerary: appreciate the extensive heritage of Malecón of Havana, get the lay of the land with Walking tours, make a trip to Paseo del Prado, and steep yourself in history at Old Square (Plaza Vieja).

For more things to do and other tourist information, you can read our Havana travel route planner.

Traveling by flight from Seven Mile Beach to Havana takes 4.5 hours. Traveling from Seven Mile Beach in December, Havana is a bit cooler at night with lows of °C. On the 15th (Tue), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Havana

Historic Sites Tours Outdoors

Side Trip

Cayo Largo
Find places to stay Dec 8 — 15:
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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