29 days in Caribbean Itinerary

29 days in Caribbean Itinerary

Created using Inspirock Caribbean route planner

Make it your trip
Fly
1
Seven Mile Beach, Cayman Islands
— 3 nights
Fly
2
Palm - Eagle Beach, Aruba
— 3 nights
Fly
3
Bridgetown, Barbados
— 3 nights
Fly
4
St. Jean, St. Barthelemy
— 3 nights
Ferry
5
Philipsburg, St. Maarten-St. Martin
— 3 nights
Fly
6
Virgin Gorda, British Virgin Islands
— 2 nights
Fly
7
Culebra, Puerto Rico
— 3 nights
Fly to Vieques, Taxi to Isla de Vieques
8
Isla de Vieques, Puerto Rico
— 3 nights
Fly
9
Puerto Plata, Dominican Republic
— 2 nights
Fly
10
Providenciales, Turks and Caicos
— 3 nights
Fly

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Seven Mile Beach, Cayman Islands

— 3 nights
Seven Mile Beach is a long crescent of coral-sand beach on the western end of Grand Cayman island. You'll visit kid-friendly attractions like Seven Mile Beach and Stingray City Grand Cayman. There's much more to do: try out the rides at Cayman Turtle Centre: Island Wildlife Encounter, explore the historical opulence of Pedro St. James National Historic Site, explore the striking landscape at Hell Gift Store, and discover the deep blue sea with a scuba or snorkeling tour.

For more things to do, photos, traveler tips, and other tourist information, go to the Seven Mile Beach tour planner.

New York City, USA to Seven Mile Beach is an approximately 8-hour flight. Prepare for much hotter weather when traveling from New York City in February: high temperatures in Seven Mile Beach hover around 84°F and lows are around 74°F. On the 2nd (Tue), wrap the sightseeing up by early afternoon so you can travel to Palm - Eagle Beach.

Things to do in Seven Mile Beach

Parks · Wildlife · Outdoors · Theme Parks

Side Trips

Find places to stay Feb 27 — Mar 2:

Palm - Eagle Beach, Aruba

— 3 nights
A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
Family-friendly places like Eagle Beach and California Lighthouse will thrill your kids. Change things up with a short trip to Baby Beach in San Nicolas (about 48 minutes away). There's more to do: kick back and relax at Palm Beach and stroll through Donkey Sanctuary Aruba.

To find ratings, photos, where to stay, and other tourist information, refer to the Palm - Eagle Beach trip itinerary maker.

You can fly from Seven Mile Beach to Palm - Eagle Beach in 9 hours. Traveling from Seven Mile Beach to Palm - Eagle Beach, you'll lose 1 hour due to the time zone difference. In March, daily temperatures in Palm - Eagle Beach can reach 88°F, while at night they dip to 78°F. Wrap up your sightseeing by early afternoon on the 5th (Fri) to allow time for travel to Bridgetown.

Things to do in Palm - Eagle Beach

Parks · Beaches · Outdoors · Wildlife

Side Trips

Find places to stay Mar 2 — 5:

Bridgetown, Barbados

— 3 nights
Bridgetown is the capital and largest city of Barbados. Kids will enjoy Harrison's Cave. and Boat Tours & Water Sports. Explore Bridgetown's surroundings by going to Saint Philip Parish (Bottom Bay & Foul Bay). Next up on the itinerary: admire the natural beauty at Andromeda Botanic Gardens, see the interesting displays at Sunbury Plantation House, tour the pleasant surroundings at Soup Bowl, and kick back and relax at Carlisle Bay.

For traveler tips, photos, maps, and more tourist information, go to the Bridgetown road trip app.

You can fly from Palm - Eagle Beach to Bridgetown in 9.5 hours. In March in Bridgetown, expect temperatures between 85°F during the day and 75°F at night. Wrap up your sightseeing on the 8th (Mon) early enough to travel to St. Jean.

Things to do in Bridgetown

Parks · Outdoors · Beaches · Tours

Side Trips

Find places to stay Mar 5 — 8:

St. Jean, St. Barthelemy

— 3 nights
Family-friendly places like St. Jean Beach and Grand Cul de Sac Beach will thrill your kids.

Plan my St. Jean trip by asking Inspirock to come up with tips and suggestions.

Getting from Bridgetown to St. Jean by flight takes about 7.5 hours. Cap off your sightseeing on the 11th (Thu) early enough to catch the ferry to Philipsburg.

Things to do in St. Jean

Beaches · Outdoors · Parks · Shopping

Side Trips

Find places to stay Mar 8 — 11:

Philipsburg, St. Maarten-St. Martin

— 3 nights
Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Kids will enjoy Orient Bay Beach and Dawn Beach. Go for a jaunt from Philipsburg to Cupecoy Bay to see Cupecoy Bay Beach about 30 minutes away. There's much more to do: enjoy the sand and surf at Maho Beach, contemplate the long history of Fort Amsterdam, contemplate the waterfront views at Mullet Bay Beach, and stop by Natural Elements.

To find maps, other places to visit, and more tourist information, go to the Philipsburg holiday website.

Traveling by ferry from St. Jean to Philipsburg takes 2 hours. Alternatively, you can fly. March in Philipsburg sees daily highs of 83°F and lows of 75°F at night. Cap off your sightseeing on the 14th (Sun) early enough to travel to Virgin Gorda.

Things to do in Philipsburg

Outdoors · Parks · Beaches · Nature

Side Trips

Find places to stay Mar 11 — 14:

Virgin Gorda, British Virgin Islands

— 2 nights
Thankfully lacking some of the commercialism of other islands nearby, Virgin Gorda offers a relaxing place to holiday, and maintains a feeling of intimacy despite its reputation as an exclusive destination.
Kick off your visit on the 15th (Mon): kick back and relax at Spring Bay, tour the pleasant surroundings at The Baths, and then stroll through Savannah Bay. On the next day, stroll through Biras Creek Trail and then stroll through Honeymoon Beach.

To find photos, where to stay, traveler tips, and other tourist information, refer to the Virgin Gorda trip itinerary planner.

Getting from Philipsburg to Virgin Gorda by flight takes about 4 hours. Expect a daytime high around 84°F in March, and nighttime lows around 75°F. Finish your sightseeing early on the 16th (Tue) so you can travel to Culebra.

Things to do in Virgin Gorda

Outdoors · Parks · Beaches · Nature
Find places to stay Mar 14 — 16:

Culebra, Puerto Rico

— 3 nights

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Family-friendly places like Flamenco Beach and Melones Beach will thrill your kids. Next up on the itinerary: kick back and relax at Zoni Beach, tour the pleasant surroundings at Playa Punta Soldado Beach, step off the mainland to explore Culebrita Island, and enjoy the sea views from Culebrita Lighthouse.

For maps, other places to visit, reviews, and more tourist information, go to the Culebra trip itinerary planning tool.

Traveling by flight from Virgin Gorda to Culebra takes 5.5 hours. In March, daytime highs in Culebra are 84°F, while nighttime lows are 73°F. Cap off your sightseeing on the 19th (Fri) early enough to travel to Isla de Vieques.

Things to do in Culebra

Parks · Beaches · Outdoors · Nature
Find places to stay Mar 16 — 19:

Isla de Vieques, Puerto Rico

— 3 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.
Bring the kids along to Sun Bay Beach and Media Luna Beach. The adventure continues: stroll through Vieques National Wildlife Refuge, enjoy the sand and surf at Secret Beach (Pata Prieta), and take a leisurely stroll along Mosquito Pier.

To find where to stay, more things to do, reviews, and tourist information, you can read our Isla de Vieques trip planner.

You can do a combination of flight and taxi from Culebra to Isla de Vieques in 3 hours. Alternatively, you can do a combination of flight, car, and ferry; or ride a ferry. Expect a daytime high around 84°F in March, and nighttime lows around 72°F. Wrap up your sightseeing on the 22nd (Mon) early enough to travel to Puerto Plata.

Things to do in Isla de Vieques

Parks · Beaches · Outdoors · Wildlife
Find places to stay Mar 19 — 22:

Puerto Plata, Dominican Republic

— 2 nights
Although out of fashion in the past decades, major revitalization efforts have made a trip to Puerto Plata a growingly popular option for the adventurous travelers.
Kick off your visit on the 23rd (Tue): stop by Estrella Avenida, then take in the dramatic scenery at 27 Charcos, and then kick back and relax at Cofresi Beach. Keep things going the next day: steep yourself in history at Fortaleza San Felipe, then ride a horse along Rancho Lorilar, and then take your sightseeing to a higher altitude at Pico Isabel de Torres.

For ratings, reviews, other places to visit, and more tourist information, use the Puerto Plata attractions tool.

Fly from Isla de Vieques to Puerto Plata in 7 hours. Alternatively, you can do a combination of ferry, taxi, and bus; or do a combination of ferry, taxi, shuttle, and bus. Traveling from Isla de Vieques in March, Puerto Plata is slightly colder at night with lows of 67°F. Wrap up your sightseeing on the 24th (Wed) early enough to travel to Providenciales.

Things to do in Puerto Plata

Parks · Nature · Outdoors · Beaches
Find places to stay Mar 22 — 24:

Providenciales, Turks and Caicos

— 3 nights
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Bring the kids along to Grace Bay Beach and Provo Golf Club. Next up on the itinerary: tour the pleasant surroundings at Taylor Bay Beach, explore the activities along Sapodilla Bay Beach, steep yourself in history at Cheshire Hall Plantation, and see the vivid underwater world at Coral Gardens Reef.

For traveler tips, reviews, more things to do, and more tourist information, you can read our Providenciales driving holiday planner.

Getting from Puerto Plata to Providenciales by flight takes about 5.5 hours. Due to the time zone difference, you'll gain 1 hour traveling from Puerto Plata to Providenciales. Plan for a bit warmer nights when traveling from Puerto Plata in March since evenings lows in Providenciales dip to 74°F. Finish your sightseeing early on the 27th (Sat) so you can travel back home.

Things to do in Providenciales

Parks · Outdoors · Beaches · Nature

Side Trip

Find places to stay Mar 24 — 27: