57 days in Caribbean Itinerary

57 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary planner

Plan created by another user.Make it yours

Route & dates

1
Havana, Cuba
— 8 nights
2
Providenciales, Turks and Caicos
— 5 nights
3
Punta Cana, Dominican Republic
— 10 nights
4
Culebra, Puerto Rico
— 6 nights
5
Isla de Vieques, Puerto Rico
— 10 nights
6
Shoal Bay Village, Anguilla
— 4 nights
7
Willemstad, Curacao
— 7 nights
8
Palm - Eagle Beach, Aruba
— 6 nights

8
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Family-friendly places like Malecón of Havana and Plaza de la Catedral will thrill your kids. Change things up with these side-trips from Havana: Cuevas de Bellamar (in Matanzas) and Cayo Largo (Punta Mal Tiempo & Sirena Beach). And it doesn't end there: appreciate the extensive heritage of Old Havana, get the lay of the land with Walking tours, contemplate the long history of Fortaleza de San Carlos de la Cabana, and don't miss a visit to El Capitolio.

To see more things to do, other places to visit, photos, and more tourist information, refer to the Havana trip builder.

Stockholm, Sweden to Havana is an approximately 16.5-hour flight. The time zone changes from Central European Standard Time to Cuba Standard Time, which is usually a -6 hour difference. Traveling from Stockholm in November, things will get warmer in Havana: highs are around °C and lows about °C. Finish up your sightseeing early on the 13th (Fri) so you can travel to Providenciales.

Things to do in Havana

Historic Sites Parks Tours

Side Trips

Cayo Largo, Cuevas de Bellamar
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Sirena Beach ©
Sirena Beach

5
nights
Providenciales, Turks and Caicos

Providenciales ©
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 Little Water Cay. Next up on the itinerary: tour the pleasant surroundings at Taylor Bay Beach, kick back and relax at Malcolm's Road Beach, make a trip to Leeward Beach, and explore the activities along Sapodilla Bay Beach.

To find ratings, other places to visit, maps, and tourist information, refer to the Providenciales trip planning website.

You can fly from Havana to Providenciales in 7.5 hours. Expect a bit warmer evenings in Providenciales when traveling from Havana in November, with lows around °C. Wrap up your sightseeing on the 18th (Wed) to allow time to travel to Punta Cana.

Things to do in Providenciales

Parks Outdoors Beaches

Side Trip

Smith's Reef
Highlights from your plan
Grace Bay Beach ©
Grace Bay Beach
Provo Golf Club ©
Provo Golf Club
Half Moon Bay ©
Half Moon Bay

10
nights
Punta Cana, Dominican Republic

Punta Cana ©
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.
Family-friendly places like Bavaro Beach and Swim with Dolphins will thrill your kids. Explore Punta Cana's surroundings by going to Conquista Park (in Bayahibe) and La Romana (Altos de Chavon & Teeth Of The Dog). Spend a day of island exploring on the 20th (Fri) at Saona Island. Spend the 27th (Fri) exploring nature at National Park of the East. There's much more to do: tour the pleasant surroundings at Macao Beach, find something for the whole family at Manati Park Bavaro, explore the activities along Hoyo Azul, and look for gifts at La Perla Dominicana.

To see other places to visit, ratings, traveler tips, and more tourist information, read our Punta Cana trip planning tool.

Getting from Providenciales to Punta Cana by flight takes about 6.5 hours. Traveling from Providenciales to Punta Cana, you'll lose 1 hour due to the time zone difference. Expect a daytime high around °C in November, and nighttime lows around °C. Finish up your sightseeing early on the 28th (Sat) so you can travel to Culebra.

Things to do in Punta Cana

Outdoors Parks Tours

Side Trips

La Romana, La Altagracia Province, Conquista Park
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Manati Park Bavaro ©
Manati Park Bavaro
Macao Beach ©
Macao Beach

6
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.
Attractions like Flamenco Beach and Culebra National Wildlife Refuge make great kid-friendly stops. The adventure continues: step off the mainland to explore Culebrita Island, enjoy the sand and surf at Brava Beach, tour the pleasant surroundings at Zoni Beach, and take a memorable tour with Tours.

To see photos, other places to visit, where to stay, and tourist information, refer to the Culebra route planner.

You can fly from Punta Cana to Culebra in 6.5 hours. Other options are to do a combination of bus, ferry, and taxi; or do a combination of bus, ferry, and shuttle. In November, daily temperatures in Culebra can reach °C, while at night they dip to °C. Finish your sightseeing early on the 4th (Fri) so you can travel to Isla de Vieques.

Things to do in Culebra

Parks Outdoors Beaches
Highlights from your plan
Culebrita Island ©
Culebrita Island
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach

10
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.
Bring the kids along to La Chiva and Sun Bay Beach. There's lots more to do: enjoy some diversion at Vieques Gun Club & Sporting Clays, view the masterpieces at Siddhia Hutchinson Fine Art Gallery, expand your understanding of the military at Camp Garcia, and enjoy the sand and surf at La Plata Beach.

To see ratings, more things to do, traveler tips, and tourist information, go to the Isla de Vieques trip planner.

Drive from Culebra to Isla de Vieques in 4 hours. Alternatively, you can ride a ferry. In December, plan for daily highs up to °C, and evening lows to °C. Cap off your sightseeing on the 14th (Mon) early enough to travel to Shoal Bay Village.

Things to do in Isla de Vieques

Parks Outdoors Beaches
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
Media Luna Beach ©
Media Luna Beach
La Chiva ©
La Chiva

4
nights
Shoal Bay Village, Anguilla

Shoal Bay Village ©
You'll visit kid-friendly attractions like Shoal Bay and Maundays Bay. Go for a jaunt from Shoal Bay Village to West End Village to see Limin' Boutique about 38 minutes away.

Plan a Shoal Bay Village trip in moments using our itinerary builder.

You can fly from Isla de Vieques to Shoal Bay Village in 5.5 hours. Expect a daytime high around °C in December, and nighttime lows around °C. Finish your sightseeing early on the 18th (Fri) so you can travel to Willemstad.

Things to do in Shoal Bay Village

Parks Outdoors Beaches

Side Trips

Anguilla, Sandy Ground, West End Village, The Valley, Meads Bay
Highlights from your plan
Maundays Bay ©
Maundays Bay
Shoal Bay ©
Shoal Bay
Rendezvous Bay Beach ©
Rendezvous Bay Beach

7
nights
Willemstad, Curacao

Willemstad is the capital city of Curaçao, an island in the southern Caribbean Sea that forms a constituent country of the Kingdom of the Netherlands. Attractions like Queen Emma Pontoon Bridge and Cas Abao Beach make great kid-friendly stops. There's lots more to do: see some colorful creatures with a scuba or snorkeling tour, contemplate the waterfront views at Kleine Knip, examine the collection at Mikve Israel-Emanuel Synagogue, and enjoy the sand and surf at Mambo Beach.

For ratings, reviews, photos, and tourist information, use the Willemstad trip itinerary maker app.

Traveling by combination of ferry and flight from Shoal Bay Village to Willemstad takes 6.5 hours. Alternatively, you can fly. Expect a daytime high around °C in December, and nighttime lows around °C. Wrap up your sightseeing on the 25th (Fri) to allow time to travel to Palm - Eagle Beach.

Things to do in Willemstad

Parks Outdoors Beaches

Side Trip

Curacao
Highlights from your plan
Scuba & Snorkeling
Cas Abao Beach ©
Cas Abao Beach
Playa PortoMari ©
Playa PortoMari

6
nights
Palm - Eagle Beach, Aruba

Palm - Eagle Beach ©
A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
Kids will enjoy Eagle Beach and Palm Beach. Explore the numerous day-trip ideas around Palm - Eagle Beach: San Nicolas (Baby Beach & Rodgers Beach). And it doesn't end there: explore the wealth of natural beauty at Arikok National Park, kick back and relax at Arashi Beach, explore the striking landscape at Ayo and Casibari Rock Formations, and tour the pleasant surroundings at Boca Cataavlina.

For ratings, traveler tips, and tourist information, you can read our Palm - Eagle Beach vacation builder app.

You can fly from Willemstad to Palm - Eagle Beach in 4.5 hours. In December, daytime highs in Palm - Eagle Beach are °C, while nighttime lows are °C. Wrap up your sightseeing on the 31st (Thu) to allow time to travel back home.

Things to do in Palm - Eagle Beach

Parks Outdoors Beaches

Side Trips

Noord, Santa Cruz, Oranjestad, San Nicolas, Ayo and Casibari Rock Formations
Highlights from your plan
Eagle Beach ©
Eagle Beach
Palm Beach ©
Palm Beach
Baby Beach ©
Baby Beach

Similar Plans

9 days in Caribbean BY A USER FROM UNITED STATES June, outdoors, relaxing, beaches, historic sites, shopping, wildlife, slow & easy, popular & hidden gems Preferences: June, outdoors, relaxing, beaches, historic sites, shopping, wildlife Attraction style: Popular & hidden gems Pace: Slow & easy 9 days in Caribbean BY A USER FROM UNITED STATES July, teens, culture, outdoors, relaxing, beaches, historic sites, wildlife, popular & hidden gems Preferences: July, teens, culture, outdoors, relaxing, beaches, historic sites, wildlife Attraction style: Popular & hidden gems Pace: Medium 9 days in Caribbean BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, wildlife, hidden gems Preferences: September, culture, outdoors, relaxing, romantic, beaches, wildlife Attraction style: Hidden gems Pace: Medium 10 days in Caribbean & Saba BY A USER FROM UNITED STATES July, teens, culture, outdoors, relaxing, beaches, historic sites, wildlife, popular & hidden gems Preferences: July, teens, culture, outdoors, relaxing, beaches, historic sites, wildlife Attraction style: Popular & hidden gems Pace: Medium 10 days in Caribbean, South America & Central America BY A USER FROM UNITED STATES July, teens, culture, outdoors, relaxing, beaches, historic sites, wildlife, hidden gems Preferences: July, teens, culture, outdoors, relaxing, beaches, historic sites, wildlife Attraction style: Hidden gems Pace: Medium 15 days in Caribbean BY A USER FROM UNITED STATES August, teens, outdoors, relaxing, beaches, shopping, popular & hidden gems Preferences: August, teens, outdoors, relaxing, beaches, shopping Attraction style: Popular & hidden gems Pace: Medium 8 days in Caribbean BY A USER FROM UNITED STATES May, culture, relaxing, romantic, beaches, historic sites, shopping, popular sights Preferences: May, culture, relaxing, romantic, beaches, historic sites, shopping Attraction style: Popular sights Pace: Medium 9 days in Central America & Caribbean BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, beaches, historic sites, wildlife, popular & hidden gems Preferences: June, culture, outdoors, relaxing, beaches, historic sites, wildlife Attraction style: Popular & hidden gems Pace: Medium 8 days in Caribbean BY A USER FROM UNITED STATES March, outdoors, relaxing, beaches, historic sites, popular & hidden gems Preferences: March, outdoors, relaxing, beaches, historic sites Attraction style: Popular & hidden gems Pace: Medium 25 days in Belize, Caribbean & Panama City BY A USER FROM NORWAY May, culture, relaxing, beaches, shopping, popular sights Preferences: May, culture, relaxing, beaches, shopping Attraction style: Popular sights Pace: Medium 31 days in Caribbean BY A USER FROM CANADA April, slow & easy, hidden gems Preferences: April Attraction style: Hidden gems Pace: Slow & easy 10 days in Caribbean BY A USER FROM UNITED STATES December, culture, outdoors, relaxing, romantic, popular sights Preferences: December, culture, outdoors, relaxing, romantic Attraction style: Popular sights Pace: Medium
See more plans