39 days in Caribbean Itinerary

39 days in Caribbean Itinerary

Created using Inspirock Caribbean travel route planner

Plan created by another user. Make it yours
Fly
1
San Juan, Puerto Rico
— 4 nights
Drive
2
Ponce, Puerto Rico
— 3 nights
Drive to Ceiba, Puerto Rico, Ferry to Culebra
3
Culebra, Puerto Rico
— 2 nights
Fly to Vieques, Drive to Isla de Vieques
4
Isla de Vieques, Puerto Rico
— 2 nights
Fly
5
St. Croix, U.S. Virgin Islands
— 3 nights
Fly to Charlotte Amalie, Taxi to Charlotte Amalie
6
Charlotte Amalie, U.S. Virgin Islands
— 5 nights
Ferry to Cruz Bay, St John, Drive to Virgin Islands National Park
7
Virgin Islands National Park, U.S. Virgin Islands
— 2 nights
+2
Drive to Cruz Bay, St John, Ferry to Red Hook, St Thomas, Fly to St. George
8
Hamilton, Bermuda
— 6 nights
Fly
9
Grand Bahama Island, Bahamas
— 3 nights
Fly
10
Nassau, Bahamas
— 3 nights
Ferry
11
Harbour Island, Bahamas
— 2 nights
Ferry to Nassau, Fly to Governors Harbour
12
Eleuthera, Bahamas
— 3 nights
Fly

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4
nights
San Juan, Puerto Rico

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Your day by day itinerary now includes La Fortaleza - Palacio de Santa Catalina, Casa Blanca Museum, Botanical Garden in Rio Piedras, and other attractions you added. It doesn't end there: appreciate the extensive heritage of Old San Juan and contemplate the long history of Sitio Histórico de San Juan.

To see where to stay, maps, photos, and other tourist information, use the San Juan online travel route planner.

Miami, USA to San Juan is an approximately 6-hour flight. You'll lose 1 hour traveling from Miami to San Juan due to the time zone difference. Traveling from Miami in November, San Juan is somewhat warmer at night with lows of 76°F. Finish your sightseeing early on the 24th (Sun) to allow enough time to drive to Ponce.

Things to do in San Juan

Parks · Historic Sites · Wildlife · Nature

Side Trip

Find places to stay Nov 20 — 24:

3
nights
Ponce, Puerto Rico

Ponce is both a city and a municipality in the southern part of Puerto Rico. Your list of things to see and do now includes Cathedral of our Lady of Guadaloupe, Ponce History Museum, La Parguera, and other attractions. Next up on the itinerary: take an in-depth tour of Museo de Arte de Ponce, admire the striking features of Casa Wiechers-Villaronga, take in the waterfront at La Guancha, and make a trip to Plaza de las Delicias.

For maps, where to stay, ratings, and tourist information, read our Ponce day trip tool.

Traveling by car from San Juan to Ponce takes 1.5 hours. Alternatively, you can take a shuttle. Traveling from San Juan in November, you will find days in Ponce are a bit cooler (82°F), and nights are about the same (73°F). Finish your sightseeing early on the 27th (Wed) so you can travel to Culebra.

Things to do in Ponce

Museums · Historic Sites · Neighborhoods · Outdoors

Side Trips

Find places to stay Nov 24 — 27:

2
nights
Culebra, Puerto Rico

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
On the 27th (Wed), enjoy the sand and surf at Flamenco Beach. Here are some ideas for day two: kick back and relax at Zoni Beach, see the interesting displays at Museo Historico de Culebra, then step off the mainland to explore Culebrita Island, and finally enjoy the sea views from Culebrita Lighthouse.

To find ratings, other places to visit, maps, and tourist information, read Culebra trip maker tool.

Traveling by combination of car and ferry from Ponce to Culebra takes 4 hours. Alternatively, you can do a combination of shuttle and flight; or do a combination of car, bus, taxi, and ferry. In November, daily temperatures in Culebra can reach 86°F, while at night they dip to 76°F. Wrap up your sightseeing on the 29th (Fri) early enough to travel to Isla de Vieques.

Things to do in Culebra

Parks · Outdoors · Beaches · Nature
Find places to stay Nov 27 — 29:

2
nights
Isla de Vieques, Puerto Rico

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.
Bioluminescent Mosquito Bay has been added to your itinerary. Start off your visit on the 29th (Fri): enjoy the sand and surf at La Chiva, then take a leisurely stroll along Mosquito Pier, and then contemplate the waterfront views at Bioluminescent Mosquito Bay. On the 30th (Sat), you'll have a packed day of sightseeing: explore the activities along Sun Bay Beach and then take a leisurely stroll along Malecon.

To find photos, more things to do, where to stay, and other tourist information, you can read our Isla de Vieques trip itinerary planning website.

You can do a combination of flight and car from Culebra to Isla de Vieques in 4 hours. Another option is to ride a ferry. In November in Isla de Vieques, expect temperatures between 86°F during the day and 75°F at night. Finish up your sightseeing early on the 1st (Sun) so you can travel to St. Croix.

Things to do in Isla de Vieques

Parks · Outdoors · Beaches · Nature
Find places to stay Nov 29 — Dec 1:

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

Twin City

The largest of the U.S.
Your day by day itinerary now includes St. George Village Botanical Garden, Old Danish School, Frederiksted, and other attractions you added. There's more to do: steep yourself in history at Fort Christiansvaern and appreciate the history behind Point Udall.

To find where to stay, traveler tips, reviews, and tourist information, you can read our St. Croix day trip tool.

Traveling by flight from Isla de Vieques to St. Croix takes 3.5 hours. In December, plan for daily highs up to 85°F, and evening lows to 74°F. Finish your sightseeing early on the 4th (Wed) to allow enough time to travel to Charlotte Amalie.

Things to do in St. Croix

Parks · Historic Sites · Wildlife · Outdoors
Find places to stay Dec 1 — 4:

5
nights

Duty-free Capital of the World

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.
You've added 99 Steps, Three Queens Statue, A.H. Riise Mall, and other attractions to your itinerary. There's still lots to do: enjoy the sand and surf at Magens Bay, steep yourself in history at Blackbeard’s Castle, take some stellar pictures from Charlotte Amalie Overlook, and get engrossed in the history at St. Thomas Historical Trust Museum.

To see traveler tips, other places to visit, more things to do, and tourist information, read our Charlotte Amalie tour itinerary planning website.

You can do a combination of flight and taxi from St. Croix to Charlotte Amalie in 2.5 hours. Alternatively, you can ride a ferry. Expect a daytime high around 85°F in December, and nighttime lows around 75°F. Wrap up your sightseeing on the 9th (Mon) to allow time to travel to Virgin Islands National Park.

Things to do in Charlotte Amalie

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Find places to stay Dec 4 — 9:

2
nights

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.
You've added Cinnamon Bay Beach, Reef Bay Trail, Salt Pond Bay, and other attractions to your itinerary. On the 9th (Mon), get your bearings at Cruz Bay Visitor Center, enjoy the sand and surf at Trunk Bay Beach, and then enjoy the sand and surf at Salt Pond Bay. Get ready for a full day of sightseeing on the next day: trek along Reef Bay Trail and then enjoy the sand and surf at Cinnamon Bay Beach.

To see where to stay, reviews, maps, and tourist information, read our Virgin Islands National Park trip planning app.

Do a combination of ferry and car from Charlotte Amalie to Virgin Islands National Park in 1.5 hours. In December, daily temperatures in Virgin Islands National Park can reach 85°F, while at night they dip to 75°F. Wrap up your sightseeing on the 11th (Wed) early enough to travel to Hamilton.

Things to do in Virgin Islands National Park

Outdoors · Parks · Beaches · Trails
Find places to stay Dec 9 — 11:

6
nights
Hamilton, Bermuda

Hamilton is the capital of the British Overseas Territory of Bermuda. You've added Palm Grove, St. George's Historical Society Museum, Bermuda Botanical Gardens, and other attractions to your itinerary. Get out of town with these interesting Hamilton side-trips: St. George (Tobacco Bay, The Unfinished Church, &more). There's still lots to do: get to know the resident critters at Bermuda Aquarium, Natural History Museum & Zoo, wander the streets of Front Street, and kick back and relax at Elbow Beach.

Discover how to plan a Hamilton trip in just a few steps with Inspirock's itinerary builder.

You can do a combination of car, ferry, and flight from Virgin Islands National Park to Hamilton in 11 hours. Plan for little chillier temperatures traveling from Virgin Islands National Park in December, with highs in Hamilton at 72°F and lows at 64°F. Cap off your sightseeing on the 17th (Tue) early enough to travel to Grand Bahama Island.

Things to do in Hamilton

Parks · Outdoors · Museums · Historic Sites

Side Trips

Find places to stay Dec 11 — 17:

3
nights
Grand Bahama Island, Bahamas

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. On the 17th (Tue), don't miss a visit to Count Basie Square. On the 18th (Wed), you'll have a packed day of sightseeing: take in nature's colorful creations at Garden of the Groves, step into the grandiose world of Cooper's Castle, and then buy something for everyone on your list at Port Lucaya Marketplace.

For more things to do, maps, traveler tips, and more tourist information, refer to the Grand Bahama Island vacation maker app.

Traveling by flight from Hamilton to Grand Bahama Island takes 11 hours. The time zone changes from Atlantic Standard Time to Eastern Standard Time, which is usually a -1 hour difference. 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. Wrap up your sightseeing on the 20th (Fri) to allow time to travel to Nassau.

Things to do in Grand Bahama Island

Parks · Wildlife · Outdoors · Shopping
Find places to stay Dec 17 — 20:

3
nights
Nassau, Bahamas

On a trip to Nassau you can immerse yourself in a dynamic city atmosphere or spend your days lazing on the soft golden sands.
You've added Bahamas Historical Society, Bay Street, Balcony House, and other attractions to your itinerary. There's more to do: get up close and personal with brilliant marine life at Marine Habitat at Atlantis and kick back and relax at Cable Beach.

For maps, ratings, reviews, and other tourist information, read our Nassau online trip planner.

Fly from Grand Bahama Island to Nassau in 3.5 hours. Alternatively, you can ride a ferry. In December, daily temperatures in Nassau can reach 82°F, while at night they dip to 69°F. On the 23rd (Mon), wrap the sightseeing up by early afternoon so you can ride a ferry to Harbour Island.

Things to do in Nassau

Parks · Museums · Historic Sites · Zoos & Aquariums

Side Trip

Find places to stay Dec 20 — 23:

2
nights
Harbour Island, Bahamas

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.
Pink Sands Beach has been added to your itinerary.

Use Inspirock's suggestions to plan your Harbour Island trip and find the best activities and attractions for your vacation.

You can ride a ferry from Nassau to Harbour Island in 3.5 hours. Finish your sightseeing early on the 25th (Wed) so you can travel to Eleuthera.

Things to do in Harbour Island

Outdoors · Beaches · Parks · Shopping
Find places to stay Dec 23 — 25:

3
nights
Eleuthera, Bahamas

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: explore the wealth of natural beauty at Leon Levy Native Plant Preserve, kick back and relax at Lighthouse Beach, tour the pleasant surroundings at French Leave Beach, and get your bearings at Haynes Library.

To find photos, where to stay, maps, and other tourist information, go to the Eleuthera holiday planner.

Traveling by combination of ferry and flight from Harbour Island to Eleuthera takes 6.5 hours. Alternatively, you can do a combination of ferry and taxi; or ride a ferry. Wrap up your sightseeing on the 28th (Sat) early enough to travel back home.

Things to do in Eleuthera

Parks · Outdoors · Beaches · Nature
Find places to stay Dec 25 — 28:

Puerto Rico travel guide

4.5
Historic Walking Areas · Beaches · Forests
A U.S. territory encompassing one big island and several smaller ones, Puerto Rico appeals to visitors from around the globe with its rich history, pleasant climate, natural beauty, and renowned local cuisine. Most tourists take a vacation in Puerto Rico for that classic seaside experience, though the island offers much more than just sun and sand. Tours of Puerto Rico usually start in the city of San Juan, which boasts a trendy bar scene and plenty of art museums for visitors looking to add a bit of culture to their vacation. A short drive from the island's urban centers, pristine rainforests serve as peaceful retreats from the city bustle and ensure plenty of chances to spot wildlife and take exhilarating nature walks.

St. Thomas travel guide

4.2
Beaches · Gift & Specialty Shops · Scuba & Snorkeling
Plan a trip to St. Thomas for a holiday full of duty-free shopping, relaxing, and sightseeing. Although the most commercialized of the U.S. Virgin Islands, St. Thomas is rich in culture and history. A popular cruise ship destination, the hilly island boasts idyllic beaches, upscale resorts, a lively nightlife, and a fine dining scene. Whether you're looking to visit churches and museums, laze on tropical beaches, or have an outdoor adventure, you won't run out of things to do on St. Thomas.

St. John travel guide

4.8
Beaches · Kayaking & Canoeing · Gift & Specialty Shops
With two thirds of St. John designated as a national park, the smallest of the U.S. Virgin Islands is also the least developed, lacking an airport and cruise ship docks. Although well connected to its more commercialized neighbor, St. Thomas, St. John makes it easy to get away from crowds and enjoy pristine white-sand beaches. On a trip to St. John you can spend your days snorkeling or kayaking, explore the verdant hills of the national park, or head to Cruz Bay, the islands largest town, for excellent dining and shopping.

Bermuda travel guide

4.1
Beaches · Caves · Scenic Walking Areas
The tropical "island" of Bermuda is actually a number of islands connected by road bridges and surrounded by numerous islets and cays. With access to everything from upscale resorts and quaint seaside inns, to tranquil pink-sand beaches and secluded snorkeling spots, a holiday in Bermuda appeals to most vacationers, regardless of age or budget. Although known as a place to relax, you'll find plenty of things to do in Bermuda. Partake in dynamic nightlife of the capital city, explore scenic hiking trails, or roam the narrow streets of St. George, the oldest British town in the New World.