60 days in Caribbean Itinerary

60 days in Caribbean Itinerary

Created using Inspirock Caribbean trip planner

Make it your trip
Fly
1
Punta Cana, Dominican Republic
— 7 nights
Shuttle
2
Santo Domingo, Dominican Republic
— 5 nights
Drive
3
Puerto Plata, Dominican Republic
— 5 nights
Drive
4
Milot, Haiti
— 1 night
Drive
5
Port-au-Prince, Haiti
— 4 nights
Fly
6
Providenciales, Turks and Caicos
— 7 nights
Fly
7
Cockburn Town, Turks and Caicos
— 4 nights
Fly
8
Nassau, Bahamas
— 6 nights
Taxi
9
Paradise Island, Bahamas
— 5 nights
Taxi to Nassau, Fly to Grand Bahama Island
10
Grand Bahama Island, Bahamas
— 4 nights
Fly
11
Havana, Cuba
— 7 nights
Drive
12
Varadero, Cuba
— 4 nights
Fly

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Punta Cana, Dominican Republic

— 7 nights
In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Relax by the water at Juanillo Beach and Tropical Treasure. Explore hidden gems such as Hoyo Azul and Arena Gorda Beach. Change things up with a short trip to Parroquia de San Dionisio in Higuey (about 42 minutes away). Spend the 8th (Tue) spotting exotic species with a safari tour. There's lots more to do: enjoy the sand and surf at Bavaro Beach, stroll through Macao Beach, head outdoors with Destiny Caribbean Tours, and tee off at Golf Punta Cana.

To see other places to visit, maps, traveler tips, and other tourist information, read Punta Cana sightseeing app.

Stockholm, Sweden to Punta Cana is an approximately 16-hour flight. The time zone difference moving from Central European Standard Time (CET) to Atlantic Standard Time (AST) is minus 5 hours. Traveling from Stockholm in June, you will find days in Punta Cana are a bit warmer (36°C), and nights are much hotter (28°C). Finish up your sightseeing early on the 8th (Tue) so you can catch the shuttle to Santo Domingo.

Things to do in Punta Cana

Outdoors · Parks · Beaches · Tours

Side Trip

Find places to stay Jun 1 — 8:
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Santo Domingo, Dominican Republic

— 5 nights
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Eschew the tourist crowds and head to Basilica Cathedral of Santa Maria la Menor and Museo Memorial de la Resistencia. Venture out of the city with trips to Centro Historico Ron Barcelo (in San Pedro de Macoris) and Playa Guayacanes (in Guayacanes). There's lots more to do: appreciate the history behind Columbus Lighthouse (Faro A Colon), steep yourself in history at Convento de los Dominicos, get a sense of history and politics at Palacio National, and relax in the rural setting at Kahkow Experience.

For photos, traveler tips, and more tourist information, refer to the Santo Domingo online trip itinerary builder.

You can take a shuttle from Punta Cana to Santo Domingo in 2 hours. Alternatively, you can drive; or fly. Wrap up your sightseeing on the 13th (Sun) early enough to drive to Puerto Plata.

Things to do in Santo Domingo

Side Trips

Find places to stay Jun 8 — 13:
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Puerto Plata, Dominican Republic

— 5 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.
Visit Playa Caleton and Beach Alicia for some beach relaxation. Explore hidden gems such as 27 Charcos and Horseback Riding Tours. The adventure continues: get up close and personal with brilliant marine life at Ocean World Adventure Park, Puerto Plata, get outside with Outdoor Activities, see Off-Road Tours, and take in the exciting artwork at Joyeria Las Americas.

For traveler tips, other places to visit, photos, and tourist information, read our Puerto Plata online itinerary planner.

Traveling by car from Santo Domingo to Puerto Plata takes 3 hours. Alternatively, you can take a bus. In June, daily temperatures in Puerto Plata can reach 38°C, while at night they dip to 26°C. Wrap up your sightseeing on the 18th (Fri) to allow time to drive to Milot.

Things to do in Puerto Plata

Outdoors · Parks · Tours · Beaches

Side Trips

Find places to stay Jun 13 — 18:
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Milot, Haiti

— 1 night
On the 19th (Sat), don't miss a visit to Citadelle Laferrière and then steep yourself in history at National History Park - Citadel, Sans Souci, Ramiers.

To see more things to do, maps, other places to visit, and other tourist information, read Milot route planner.

Drive from Puerto Plata to Milot in 4 hours. Alternatively, you can do a combination of taxi, bus, and car; or do a combination of bus and car. Due to the time zone difference, you'll gain 1 hour traveling from Puerto Plata to Milot. When traveling from Puerto Plata in June, plan for little chillier days and a bit warmer nights in Milot: temperatures range from 35°C by day to 31°C at night. Finish up your sightseeing early on the 19th (Sat) so you can go by car to Port-au-Prince.

Things to do in Milot

Historic Sites

Side Trip

Find places to stay Jun 18 — 19:
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Port-au-Prince, Haiti

— 4 nights
Port-au-Prince, the capital of Haiti, gives most visitors their first taste of the country, along with all of its rugged and lively charm.
Discover out-of-the-way places like The Bureau of Ethnology and Notre Dame Cathedral Ruins. Get out of town with these interesting Port-au-Prince side-trips: Kokoye Beach (in Petit Goave) and Rosie's Boutique (in Cabaret). And it doesn't end there: explore the galleries of Musee du Pantheon National Haitien, admire the masterpieces at El-Saieh Gallery, hunt for treasures at Marche de Fer, and indulge your thirst for a good beer at Barbancourt Rum Distillery.

To see reviews, traveler tips, other places to visit, and tourist information, refer to the Port-au-Prince trip site.

Getting from Milot to Port-au-Prince by car takes about 4 hours. Other options: do a combination of taxi and bus. When traveling from Milot in June, plan for somewhat warmer days in Port-au-Prince, with highs around 39°C, while nights are about the same with lows around 32°C. Cap off your sightseeing on the 23rd (Wed) early enough to catch the flight to Providenciales.

Things to do in Port-au-Prince

Shopping · Historic Sites · Museums · Breweries & Distilleries

Side Trips

Find places to stay Jun 19 — 23:
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Providenciales, Turks and Caicos

— 7 nights
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
You'll explore the less-touristy side of things at Long Bay Beach and Leeward Beach. Relax by the water at Grace Bay Beach and Malcolm's Road Beach. Spend the 28th (Mon) exploring nature at Princess Alexandra National Park. The adventure continues: get up close to creatures of the deep with Ocean Vibes Scuba & Watersports, stroll through Half Moon Bay, soothe aching muscles at some of the top local wellness centers, and steep yourself in history at Cheshire Hall Plantation.

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

Traveling by flight from Port-au-Prince to Providenciales takes 5 hours. In June, daily temperatures in Providenciales can reach 37°C, while at night they dip to 31°C. Finish your sightseeing early on the 30th (Wed) so you can fly to Cockburn Town.

Things to do in Providenciales

Parks · Outdoors · Beaches · Wildlife
Find places to stay Jun 23 — 30:
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Cockburn Town, Turks and Caicos

— 4 nights
Cockburn Town is the capital city of the Turks and Caicos Islands.GeographyCockburn Town is located on the largest island in the Turks Islands archipelago, Grand Turk Island. You'll discover tucked-away gems like Exclusive Escape Tours and SunRay Beach. Relax by the water at Governor's Beach and Gibbs Cay. There's much more to do: enjoy the sand and surf at Pillory Beach, head outdoors with Grand Turk Cruise Center, and browse the exhibits of Turks & Caicos National Museum.

To see reviews, where to stay, maps, and tourist information, read Cockburn Town tour app.

Traveling by flight from Providenciales to Cockburn Town takes 2.5 hours. Finish up your sightseeing early on the 4th (Sun) so you can catch the flight to Nassau.

Things to do in Cockburn Town

Outdoors · Parks · Beaches · Wildlife

Side Trips

Find places to stay Jun 30 — Jul 4:
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Nassau, Bahamas

— 6 nights
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'll discover tucked-away gems like Jaws Beach and St. Francis Xavier Cathedral. We've included these beaches for you: Cable Beach and Love Beaches. Next up on the itinerary: take a peaceful walk through Primeval Forest National Park, admire the masterpieces at The National Art Gallery of The Bahamas, examine the collection at Educulture Bahamas - Junkanoo Museum, and stroll through Dolphin Close Encounter.

To find reviews, traveler tips, photos, and other tourist information, read our Nassau trip itinerary builder.

You can fly from Cockburn Town to Nassau in 7 hours. In July, daytime highs in Nassau are 38°C, while nighttime lows are 30°C. Wrap up your sightseeing on the 10th (Sat) to allow time to drive to Paradise Island.

Things to do in Nassau

Parks · Outdoors · Beaches · Museums

Side Trip

Find places to stay Jul 4 — 10:
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Paradise Island, Bahamas

— 5 nights
Located just off the shore from the capital city, Paradise Island offers glamorous gambling, luxury living, and a welcome dose of island exploration as well.
Step off the beaten path and head to Atlantis Casino and Boat Tours & Water Sports. There's much more to do: observe the fascinating underwater world at Marine Habitat at Atlantis, explore and take pictures at Versailles Gardens and French Cloister, step off the mainland to explore Rose Island, and browse the different shops at Marina Village.

To see reviews, more things to do, ratings, and tourist information, you can read our Paradise Island sightseeing planner.

Paradise Island is very close to Nassau. July in Paradise Island sees daily highs of 38°C and lows of 30°C at night. Finish up your sightseeing early on the 15th (Thu) so you can travel to Grand Bahama Island.

Things to do in Paradise Island

Parks · Zoos & Aquariums · Nature · Casinos
Find places to stay Jul 10 — 15:
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Grand Bahama Island, Bahamas

— 4 nights
Despite its name, Grand Bahama Island isn't the biggest island in its archipelago.
Your itinerary includes some good beach time at Gold Rock Beach and Taino Beach. You'll explore the less-touristy side of things at Pat & Diane Snorkeling and Ol' Freetown Farm. Spend the 18th (Sun) exploring nature at Peterson Cay. There's more to do: enjoy the sand and surf at Fortune Beach.

For ratings, maps, photos, and tourist information, read Grand Bahama Island online trip itinerary planner.

Traveling by combination of taxi and flight from Paradise Island to Grand Bahama Island takes 3 hours. Alternatively, you can ride a ferry. In July in Grand Bahama Island, expect temperatures between 37°C during the day and 28°C at night. Cap off your sightseeing on the 19th (Mon) early enough to catch the flight to Havana.

Things to do in Grand Bahama Island

Parks · Outdoors · Beaches · Nature
Find places to stay Jul 15 — 19:
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Havana, Cuba

— 7 nights

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Discover out-of-the-way places like Nature & Wildlife Tours and Taquechel Pharmacy Museum. You'll enjoy a bit of beach vacationing at Santa Maria del Mar and Punta Mal Tiempo. Next up on the itinerary: capture your vacation like a pro with an inspiring photography tour, make a trip to Plaza de la Catedral, walk around Central Park, and steep yourself in history at Fortaleza de San Carlos de la Cabana.

To find reviews, photos, where to stay, and tourist information, use the Havana road trip site.

You can fly from Grand Bahama Island to Havana in 7 hours. In July, plan for daily highs up to 38°C, and evening lows to 26°C. Wrap up your sightseeing on the 26th (Mon) to allow time to drive to Varadero.

Things to do in Havana

Outdoors · Tours · Historic Sites · Parks

Side Trip

Find places to stay Jul 19 — 26:
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Varadero, Cuba

— 4 nights
One of the largest resort towns in the Caribbean, Varadero boasts a 20 km (12 mi) long stretch of sand, lined with hotels and all-inclusive resorts.
Visit Varadero Beach and Coral Beach - Playa Coral for some beach relaxation. You'll discover tucked-away gems like Cayos Blancos and Cueva de Saturno. It doesn't end there: don't miss a visit to Parque Central and get a dose of the wild on a nature and wildlife tour.

To find reviews, other places to visit, where to stay, and other tourist information, use the Varadero day trip site.

Traveling by car from Havana to Varadero takes 2 hours. Alternatively, you can take a shuttle; or do a combination of train and taxi. Expect a daytime high around 38°C in July, and nighttime lows around 25°C. Finish your sightseeing early on the 30th (Fri) to allow enough time to fly back home.

Things to do in Varadero

Outdoors · Parks · Beaches · Tours
Find places to stay Jul 26 — 30:
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Dominican Republic travel guide

4.1
Beaches · Islands · Zipline
Sharing the island of Hispaniola with Haiti, friendly Dominican Republic offers two distinct coastlines, one bathed by the Caribbean Sea and the other by the Atlantic Ocean. Nearly 1,600 km (1,000 mi) of palm-shaded beaches figure highly on most Dominican Republic itineraries, allowing visitors to design their vacation around a range of water-based activities. The sun-kissed country benefits from pleasant temperatures throughout the year, so it's no surprise that holidays in Dominican Republic remain a popular choice for visitors from distant and colder corners of the world. A big producer of coffee, cocoa, rum, sugarcane, and tobacco, the country provides a vibrant cultural experience in multicultural cities and quaint countryside.

Haiti travel guide

3.8
Historic Walking Areas · Historic Sites · Zipline
The culture of Haiti has always been the reason for people to visit, and it will be the reason people visit in larger and larger numbers as the nation heals from the devastating effects of the 2010 earthquake. The interesting tale of colonialism, revolution, and political struggle has left Haiti with a wealth of historical sites and cultural influences. Sightseeing in Haiti offers perspectives on the many stages in the country's history, with colonial forts standing in ruins and monuments memorializing the revolution. The music, the art, the folklore, and the cuisine of Haiti all deserve to be explored in person.

Turks and Caicos travel guide

4.5
Beaches · Scuba & Snorkeling · Landmarks
Known as the location of one of the longest coral reefs in the world, Turks and Caicos offer scenic white-sand beaches, calm waters, and warm, sunny weather. Apart from the upscale resorts in Providenciales, which is known for its award-winning beach, the rest of the scenery remains mostly pristine and uncrowded. On a trip to Turks and Caicos, you can spend days lazing on a deserted beach, go island hopping, and enjoy a range of fun activities, from world-class snorkeling and diving, to hiking, sailing, deep-sea fishing, and bird-watching.

Bahamas travel guide

3.6
Beaches · Islands · Water & Amusement Parks
Part of an archipelago encompassing hundreds of islets and cays, Bahamas boast many pink beaches, which get their vibrant color from fractured seashells mixed with ordinary sand. For most pleasure seekers an ideal holiday in Bahamas consists of various sea activities, occasionally interrupted by tours of several cities, offering an eclectic music scene dominated by calypso, soca, and junkanoo genres. Romantic enough to attract newlyweds from around the globe, the islands are also a major center of eco-tourism, with visits to national parks and diving tours in colorful reefs among the most popular things to do in Bahamas.

Cuba travel guide

4.4
Beaches · Historic Walking Areas · Landmarks
The largest island in the Caribbean, Cuba lies just 140 km (90 mi) south of Florida and captivates a growing number of Western visitors with its tropical landscapes and cultural attractions. Sightseeing in Cuba inevitably begins in Havana, a city of photogenic architecture, lively nightlife, and a passion for baseball. The country's smaller colonial towns usually feature central squares, ideal places to meet the locals under wrought-iron street lamps. Savvy visitors escape the cities during their Cuba holidays, devoting plenty of time to the country's charming countryside, where you can get the feel for this diverse land by conversing with friendly tobacco farmers and small-scale fruit producers.