40 days in Caribbean Itinerary

40 days in Caribbean Itinerary

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Route & dates

40 days in Caribbean Itinerary

Start: Auckland, New Zealand
Fly:  23​h 15​min
1
Santo Domingo, Dominican Republic
— 3 nights
Fly:  1​h 45​min
2
Philipsburg, St. Maarten-St. Martin
— 5 nights
Fly:  3​h
3
Isla de Vieques, Puerto Rico
— 8 nights
Fly:  2​h
4
San Juan, Puerto Rico
— 6 nights
Fly:  30​min
5
Culebra, Puerto Rico
— 5 nights
Fly:  7​h 45​min
6
Seven Mile Beach, Cayman Islands
— 3 nights
Fly:  2​h
7
Havana, Cuba
— 7 nights
Fly:  26​h
End: Auckland, New Zealand

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, shopping, museums, and beaches. Your plan includes some of its best attractions: don't miss a visit to Zona Colonial, pause for some photo ops at Columbus Lighthouse (Faro A Colon), contemplate the long history of Fortaleza Ozama, and step into the grandiose world of Alcazar de Colon.

To find traveler tips, ratings, and tourist information, read our Santo Domingo visit site .

Auckland, New Zealand to Santo Domingo is an approximately 23.5-hour flight. You can also do a combination of flight and shuttle; or do a combination of flight, shuttle, and bus. The time zone changes from New Zealand Standard Time to Atlantic Standard Time, which is usually a -16 hour difference. Finish your sightseeing early on the 11th (Wed) so you can travel to Philipsburg.

Things to do in Santo Domingo

Historic Sites Museums Parks
Find places to stay Nov 8 — 11:
Highlights from your plan
Alcazar de Colon ©
Alcazar de Colon
Zona Colonial ©
Zona Colonial
Catedral Primada de America
Catedral Primada de America

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, wildlife, beaches, adventure, and museums. Your plan includes some of its best attractions: enjoy the sand and surf at Maho Beach, try your luck at Casino Royale, tour the pleasant surroundings at Cupecoy Bay Beach, and explore the activities along Mullet Bay Beach.

To see maps, traveler tips, where to stay, and other tourist information, use the Philipsburg online tour itinerary maker .

Getting from Santo Domingo to Philipsburg by flight takes about 2 hours. Other options: do a combination of shuttle and flight. November in Philipsburg sees daily highs of 35°C and lows of 30°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, Maho, Sint Maarten, Saint-Martin, Paradise Peak
Find places to stay Nov 11 — 16:
Highlights from your plan
Speed Boats Tours
Maho Beach ©
Maho Beach
Orient Bay Beach ©
Orient 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, adventure, wildlife, and nightlife. Your plan includes some of its best attractions: contemplate the waterfront views at Sun Bay Beach, have fun at Vieques Gun Club & Sporting Clays, kick back and relax at La Chiva, and tour the pleasant surroundings at Media Luna Beach.

For photos, traveler tips, ratings, and tourist information, use the Isla de Vieques journey planning website .

You can fly from Philipsburg to Isla de Vieques in 3 hours. In November, plan for daily highs up to 35°C, and evening lows to 28°C. Wrap up your sightseeing on the 24th (Tue) early enough to 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
Vieques National Wildlife Refuge ©
Vieques National Wildlife Refuge
Media Luna Beach ©
Media Luna Beach

6
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Get out of town with these interesting San Juan side-trips: Ponce (Museo de Arte de Ponce & Casa Wiechers-Villaronga), Museo del Tabaco Caguas (in Caguas) and El Yunque Rain Forest (in El Yunque National Forest). There's much more to do: get to know the fascinating history of Old San Juan, take a peaceful walk through Bosque Nacional El Yunque, enjoy the sand and surf at Luquillo Beach, and indulge your taste buds at Food & Drink.

To find reviews, traveler tips, where to stay, and more tourist information, go to the San Juan trip itinerary maker site .

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. Expect a daytime high around 36°C in November, and nighttime lows around 28°C. Finish your sightseeing early on the 30th (Mon) to allow enough time to fly to Culebra.

Things to do in San Juan

Outdoors Parks Tours

Side Trips

Ponce, Luquillo Beach, Museo del Tabaco Caguas, Bosque Nacional El Yunque, El Yunque Rain Forest
Find places to stay Nov 24 — 30:
Highlights from your plan
Old San Juan ©
Old San Juan
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest

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, nature, outdoors, and adventure. Your plan includes some of its best attractions: kick back and relax at Flamenco Beach, tour the pleasant surroundings at Culebra National Wildlife Refuge, get lost in a book at Culebra Public Library, and enjoy the sea views from Culebrita Lighthouse.

For photos, reviews, maps, and more tourist information, refer to the Culebra online trip maker .

Culebra is just a stone's throw from San Juan. November in Culebra sees daily highs of 35°C and lows of 28°C at night. Wrap up your sightseeing on the 5th (Sat) early enough to 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 known for wildlife, beaches, spas, adventure, and golf. Your plan includes some of its best attractions: stroll through Stingray City Grand Cayman, laugh and play at Cayman Turtle Centre: Island Wildlife Encounter, sample the fine beverages at Cayman Spirits Co. Distillery, and step into the grandiose world of Pedro St. James National Historic Site.

For reviews, ratings, traveler tips, and more tourist information, read Seven Mile Beach trip planner.

Getting from Culebra to Seven Mile Beach by flight takes about 8 hours. Other options: do a combination of ferry, shuttle, and flight. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. In December, plan for daily highs up to 34°C, and evening lows to 28°C. Wrap up your sightseeing on the 8th (Tue) to allow time 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.
Change things up with these side-trips from Havana: Cayo Largo (Playa Paraiso & Sirena Beach). The adventure continues: don't miss a visit to Malecón of Havana, get the lay of the land with Walking tours, take an in-depth tour of Museum of the Revolution (Museo de la Revolucion), and appreciate the extensive heritage of Old Havana.

To see maps, traveler tips, where to stay, and other tourist information, you can read our Havana trip planner .

Traveling by flight from Seven Mile Beach to Havana takes 2 hours. Plan for little chillier nights when traveling from Seven Mile Beach in December since evenings lows in Havana dip to 20°C. Wrap up your sightseeing by early afternoon on the 15th (Tue) to allow time for travel back home.

Things to do in Havana

Historic Sites Tours Parks

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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