39 days in Caribbean Itinerary

39 days in Caribbean Itinerary

Created using Inspirock Caribbean travel route planner

This plan was created by another user.  Make it your plan

Route & dates

39 days in Caribbean Itinerary

Start: Miami, United States
Fly:  5​h 30​min
1
San Juan, Puerto Rico
— 4 nights
Drive:  1​h 30​min
2
Ponce, Puerto Rico
— 3 nights
shuttle + Fly:  3​h 30​min
3
Culebra, Puerto Rico
— 2 nights
Fly + Drive:  2​h 30​min
4
Isla de Vieques, Puerto Rico
— 2 nights
Fly:  1​h
5
St. Croix, U.S. Virgin Islands
— 3 nights
Fly:  1​h
6
Charlotte Amalie, U.S. Virgin Islands
— 5 nights
Drive:  1​h 30​min
7
Virgin Islands National Park, U.S. Virgin Islands
— 2 nights
+2
ferry + Drive + Fly:  12​h 30​min
8
Hamilton, Bermuda
— 6 nights
Fly:  8​h 30​min
9
Grand Bahama Island, Bahamas
— 3 nights
Fly + shuttle:  3​h 30​min
10
Nassau, Bahamas
— 3 nights
ferry:  3​h
11
Harbour Island, Bahamas
— 2 nights
+2
ferry + taxi + Fly:  5​h
12
Eleuthera, Bahamas
— 3 nights
Fly:  9​h 30​min
End: Miami, United States

4
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
You've added La Fortaleza - Palacio de Santa Catalina, Casa Blanca Museum, Museo De La Farmacia, and other attractions to your itinerary. Next up on the itinerary: get to know the fascinating history of Old San Juan and steep yourself in history at Sitio Histórico de San Juan.

To find other places to visit, maps, and tourist information, use the San Juan journey tool .

Miami, USA to San Juan is an approximately 5.5-hour flight. You can also do a combination of train and flight. You'll lose 1 hour traveling from Miami to San Juan due to the time zone difference. Traveling from Miami in November, you can expect nighttime temperatures to be somewhat warmer in San Juan, with lows of 76°F. Finish your sightseeing early on the 24th (Sun) so you can drive to Ponce.

Things to do in San Juan

Parks Historic Sites Wildlife

Side Trip

El Yunque Rain Forest
Find places to stay Nov 20 — 24:
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

3
nights
Ponce, Puerto Rico

Ponce ©
Ponce is both a city and a municipality in the southern part of Puerto Rico. Your day-by-day itinerary now includes Cathedral of our Lady of Guadaloupe, Ponce History Museum, La Parguera, and other attractions you added. There's still lots to do: explore the world behind art at Museo de Arte de Ponce, look for gifts at Plaza del Caribe, admire the landmark architecture of Casa Wiechers-Villaronga, and don't miss a visit to Plaza of Delights (Plaza de las Delicias).

To see more things to do, where to stay, reviews, and tourist information, refer to the Ponce route maker website .

Drive from San Juan to Ponce in 1.5 hours. Alternatively, you can take a shuttle. Traveling from San Juan in November, you will find days in Ponce are little chillier (82°F), and nights are about the same (73°F). Cap off your sightseeing on the 27th (Wed) early enough to travel to Culebra.

Things to do in Ponce

Museums Historic Sites Neighborhoods

Side Trips

Guayama, Palacete Los Moreau, La Parguera, Casa Dona Bisa and Museo Historia San Sebastian
Find places to stay Nov 24 — 27:
Highlights from your plan
Museo de Arte de Ponce ©
Museo de Arte de Ponce

2
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.
Start off your visit on the 27th (Wed): tour the pleasant surroundings at Flamenco Beach. On the 28th (Thu), you'll have a packed day of sightseeing: stroll through Zoni Beach, see the interesting displays at Museo Historico de Culebra, then head off the coast to Culebrita Island, and finally visit a coastal fixture at Culebrita Lighthouse.

To see maps, more things to do, and other tourist information, use the Culebra trip itinerary planning site .

You can do a combination of shuttle and flight from Ponce to Culebra in 3.5 hours. Other options are to do a combination of car and ferry; or do a combination of shuttle and ferry. In November, daytime highs in Culebra are 86°F, while nighttime lows are 76°F. Finish your sightseeing early on the 29th (Fri) to allow enough time to travel to Isla de Vieques.

Things to do in Culebra

Parks Outdoors Beaches
Find places to stay Nov 27 — 29:
Highlights from your plan
Culebrita Island ©
Culebrita Island
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach

2
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.
You've now added Bioluminescent Mosquito Bay to your itinerary. On the 29th (Fri), enjoy the sand and surf at La Chiva, then take a leisurely stroll along Mosquito Pier, and then explore the activities along Bioluminescent Mosquito Bay. Keep things going the next day: tour the pleasant surroundings at Sun Bay Beach and then take in the waterfront at Malecon.

To see where to stay, maps, other places to visit, and other tourist information, go to the Isla de Vieques route planning tool .

You can do a combination of flight and car from Culebra to Isla de Vieques in 2.5 hours. Alternatively, you can ride a ferry. Expect a daytime high around 86°F in November, and nighttime lows around 75°F. Wrap up your sightseeing on the 1st (Sun) early enough to travel to St. Croix.

Things to do in Isla de Vieques

Parks Outdoors Beaches
Find places to stay Nov 29 — Dec 1:
Highlights from your plan
Bioluminescent Mosquito Bay ©
Bioluminescent Mosquito Bay
Sun Bay Beach ©
Sun Bay Beach
Malecon ©
Malecon

3
nights
St. Croix, U.S. Virgin Islands

St. Croix ©
The largest of the U.S.
You've added St. George Village Botanical Garden, Old Danish School, Frederiksted, and other attractions to your itinerary. There's still lots to do: steep yourself in history at Fort Christiansvaern and pause for some photo ops at Point Udall.

Plan my trip to St. Croix with suggested itineraries provided by Inspirock.

Traveling by flight from Isla de Vieques to St. Croix takes an hour. Alternatively, you can do a combination of ferry, shuttle, and flight. In December, daytime highs in St. Croix are 85°F, while nighttime lows are 74°F. Cap off your sightseeing on the 4th (Wed) early enough to travel to Charlotte Amalie.

Things to do in St. Croix

Parks Historic Sites Wildlife
Find places to stay Dec 1 — 4:
Highlights from your plan
Buck Island Reef National Monument ©
Fort Christiansvaern ©
Fort Christiansvaern
Point Udall ©
Point Udall

5
nights
Charlotte Amalie, U.S. Virgin Islands

Charlotte Amalie ©
One of the most visited cruise ship destinations in the Caribbean, the town of Charlotte Amalie is known around the world for its duty-free jewelry, perfume, and liquor shops.
Your day-by-day itinerary now includes 99 Steps, Three Queens Statue, A.H. Riise Mall, and other attractions you added. There's still lots to do: kick back and relax at Magens Bay, get engrossed in the history at St. Thomas Historical Trust Museum, make a trip to Main Street, and stroll through Honeymoon Beach.

For ratings, maps, traveler tips, and tourist information, refer to the Charlotte Amalie trip itinerary maker app .

Traveling by flight from St. Croix to Charlotte Amalie takes an hour. Alternatively, you can ride a ferry. In December, plan for daily highs up to 85°F, and evening lows to 75°F. Wrap up your sightseeing on the 9th (Mon) early enough to drive to Virgin Islands National Park.

Things to do in Charlotte Amalie

Parks Outdoors Beaches

Side Trips

St. Thomas, East End, Magens Bay, Bluebeard's Hill
Find places to stay Dec 4 — 9:
Highlights from your plan
Magens Bay ©
Magens Bay
Coral World Ocean Park ©
Coral World Ocean Park
Aqua Blue Charters ©
Aqua Blue Charters

2
nights
Virgin Islands National Park, U.S. Virgin Islands

Virgin Islands National Park ©
The hills, valleys, and tropical rainforest of Virgin Islands National Park tell only half the story, with just as much (if not more) to be found under the sea.
Your day-by-day itinerary now includes Cinnamon Bay Beach, Reef Bay Trail, Salt Pond Bay, and other attractions you added. Kick off your visit on the 9th (Mon): get all the information you need at Cruz Bay Visitor Center, then stroll through Trunk Bay, and then stroll through Salt Pond Bay. Get ready for a full day of sightseeing on the next day: hike along Reef Bay Trail, examine the collection at Cinnamon Bay Archeology Museum & Lab, and then kick back and relax at Cinnamon Bay Beach.

For ratings, more things to do, traveler tips, and more tourist information, read Virgin Islands National Park tour itinerary maker tool .

Traveling by car from Charlotte Amalie to Virgin Islands National Park takes 1.5 hours. December in Virgin Islands National Park sees daily highs of 85°F and lows of 75°F at night. Finish your sightseeing early on the 11th (Wed) so you can travel to Hamilton.

Things to do in Virgin Islands National Park

Parks Outdoors Beaches
Find places to stay Dec 9 — 11:
Highlights from your plan
Trunk Bay ©
Trunk Bay
Cruz Bay Visitor Center ©
Cruz Bay Visitor Center
Salt Pond Bay ©
Salt Pond Bay

6
nights
Hamilton, Bermuda

Hamilton ©
Hamilton is the capital of the British Overseas Territory of Bermuda. Your day-by-day itinerary now includes Palm Grove, St. George's Historical Society Museum, Bermuda Botanical Gardens, and other attractions you added. You'll find plenty of places to visit near Hamilton: St. George (Tobacco Bay, The Unfinished Church, & more). And it doesn't end there: stroll through Elbow Beach, explore the galleries of Bermuda Aquarium, Natural History Museum & Zoo, and appreciate the extensive heritage of Front Street.

To find maps, other places to visit, more things to do, and more tourist information, read Hamilton journey planning website .

Explore your travel options from Virgin Islands National Park to Hamilton with the Route module. In December, Hamilton is slightly colder than Virgin Islands National Park - with highs of 72°F and lows of 64°F. Wrap up your sightseeing on the 17th (Tue) early enough to travel to Grand Bahama Island.

Things to do in Hamilton

Parks Museums Historic Sites

Side Trips

St. George, Paget Parish, Bermuda, South Shore Park, Verdmont Museum
Find places to stay Dec 11 — 17:
Highlights from your plan
Elbow Beach ©
Elbow Beach
Tobacco Bay ©
Tobacco Bay

3
nights
Grand Bahama Island, Bahamas

Grand Bahama Island ©
Despite its name, Grand Bahama Island isn't the biggest island in its archipelago.
Your day-by-day itinerary now includes Count Basie Square, Cooper's Castle and Lucayan National Park. Start off your visit on the 17th (Tue): make a trip to Count Basie Square. Keep things going the next day: admire the natural beauty at Garden of the Groves, then step into the grandiose world of Cooper's Castle, and then take a leisurely stroll along Port Lucaya Marketplace.

To find more things to do, reviews, where to stay, and tourist information, go to the Grand Bahama Island trip planner .

You can fly from Hamilton to Grand Bahama Island in 8.5 hours. The time zone difference moving from Atlantic Standard Time (AST) to Eastern Standard Time (EST) is minus 1 hour. Traveling from Hamilton in December, expect nights in Grand Bahama Island to be about the same, around 67°F, while days are a bit warmer, around 79°F. Finish your sightseeing early on the 20th (Fri) to allow enough time to travel to Nassau.

Things to do in Grand Bahama Island

Parks Wildlife Shopping
Find places to stay Dec 17 — 20:
Highlights from your plan
Garden of the Groves ©
Garden of the Groves
Gold Rock Beach ©
Gold Rock Beach
Port Lucaya Marketplace ©
Port Lucaya Marketplace

3
nights
Nassau, Bahamas

Nassau ©
On a trip to Nassau you can immerse yourself in a dynamic city atmosphere or spend your days lazing on the soft golden sands.
Your day-by-day itinerary now includes Bahamas Historical Society, Bay Street, Balcony House, and other attractions you added. The adventure continues: get up close and personal with brilliant marine life at Marine Habitat at Atlantis and kick back and relax at Cable Beach.

To see traveler tips, maps, and tourist information, read our Nassau travel route planner.

Traveling by combination of flight and shuttle from Grand Bahama Island to Nassau takes 3.5 hours. Alternatively, you can ride a ferry. December in Nassau sees daily highs of 82°F and lows of 69°F at night. Wrap up your sightseeing by early afternoon on the 23rd (Mon) to allow enough time to ride a ferry to Harbour Island.

Things to do in Nassau

Parks Zoos & Aquariums Museums

Side Trip

Paradise Island
Find places to stay Dec 20 — 23:
Highlights from your plan
Marine Habitat at Atlantis ©
Marine Habitat at Atlantis
Cable Beach ©
Cable Beach
Versailles Gardens and French Cloister ©

2
nights
Harbour Island, Bahamas

Harbour Island ©
The casual Bahamian vibee of Harbour Island comes through in its atmospheric seaside eateries, the colonial English architecture of its main urban zones, and its wealth of attractive coastal areas.
Your day-by-day itinerary now includes Pink Sands Beach.

To see where to stay, more things to do, maps, and other tourist information, read our Harbour Island online travel route planner .

Traveling by ferry from Nassau to Harbour Island takes 3 hours. Cap off your sightseeing on the 25th (Wed) early enough to travel to Eleuthera.

Things to do in Harbour Island

Parks Outdoors Beaches
Find places to stay Dec 23 — 25:
Highlights from your plan
Pink Sands Beach ©
Pink Sands Beach
Dunmore Town ©
Dunmore Town
Princess Street Gallery ©
Princess Street Gallery

3
nights
Eleuthera, Bahamas

Eleuthera ©
The long, thin island of Eleuthera has plenty of coast, built up in places and left wild and rural in others.
Your day-by-day itinerary now includes Glass Window. And it doesn't end there: stroll through Ten Bay Beach, browse the collection at Haynes Library, explore the striking landscape of Leon Levy Native Plant Preserve, and kick back and relax at Lighthouse Beach.

Inspirock's itinerary builder makes planning a Eleuthera trip simple and quick.

Traveling by combination of ferry and flight from Harbour Island to Eleuthera takes 5 hours. Alternatively, you can do a combination of ferry, flight, and taxi; or do a combination of ferry and taxi. Finish up your sightseeing early on the 28th (Sat) so you can travel back home.

Things to do in Eleuthera

Parks Outdoors Beaches
Find places to stay Dec 25 — 28:
Highlights from your plan
Lighthouse Beach ©
Lighthouse Beach
Ten Bay Beach ©
Ten Bay Beach
Haynes Library ©
Haynes Library

Similar Plans

6 days in St. Thomas BY A USER FROM UNITED STATES August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 8 days in St. Thomas BY A USER FROM UNITED STATES August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 40 days in St. Thomas BY A USER FROM UNITED STATES February, popular sights PREFERENCES: February ATTRACTION STYLE: Popular sights PACE: Medium 10 days in St. John BY A USER FROM UNITED STATES August, teens, kids, popular sights PREFERENCES: August, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 9 days in St. John BY A USER FROM UNITED STATES October, outdoors, historic sites, popular sights PREFERENCES: October, outdoors, historic sites ATTRACTION STYLE: Popular sights PACE: Medium 3 days in St. Thomas BY A USER FROM UNITED STATES August, slow & easy, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Slow & easy 12 days in St. Thomas BY A USER FROM UNITED STATES August, kids, popular sights PREFERENCES: August, kids ATTRACTION STYLE: Popular sights PACE: Medium 4 days in St. Thomas BY A USER FROM UNITED STATES February, kids, popular sights PREFERENCES: February, kids ATTRACTION STYLE: Popular sights PACE: Medium 14 days in St. Thomas BY A USER FROM UNITED STATES August, kids, popular sights PREFERENCES: August, kids ATTRACTION STYLE: Popular sights PACE: Medium 1 day in St. Thomas BY A USER FROM UNITED STATES August, kids, popular sights PREFERENCES: August, kids ATTRACTION STYLE: Popular sights PACE: Medium 9 days in St. Thomas BY A USER FROM UNITED STATES November, popular sights PREFERENCES: November ATTRACTION STYLE: Popular sights PACE: Medium 3 days in St. Croix BY A USER FROM UNITED STATES February, popular sights PREFERENCES: February ATTRACTION STYLE: Popular sights PACE: Medium
View more plans