50 days in Caribbean, United States, Mexico & Canada Itinerary

50 days in Caribbean, United States, Mexico & Canada Itinerary

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1
Isla de Vieques, Puerto Rico
— 2 nights
2
San Juan, Puerto Rico
— 3 nights
3
Punta Cana, Dominican Republic
— 3 nights
4
Santo Domingo, Dominican Republic
— 2 nights
5
Orlando, United States
— 5 nights
6
Tulum, Mexico
— 4 nights
7
Mexico City, Mexico
— 3 nights
8
Las Vegas, United States
— 5 nights
9
Chicago, United States
— 6 nights
10
Toronto, Canada
— 4 nights
11
Montreal, Canada
— 2 nights
12
Quebec City, Canada
— 4 nights
13
New York City, United States
— 6 nights

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2
nights
Isla de Vieques, Puerto Rico

Isla de Vieques ©

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.
Isla de Vieques is known for nature, beaches, and wildlife. Your plan includes some of its best attractions: get a new perspective on things with Marauder Sailing Charters - Private Tours, kick back and relax at La Chiva, trot along with a tour on horseback, and take in the waterfront at Malecon.

To see traveler tips, maps, and tourist information, read our Isla de Vieques trip planner.

Philadelphia, USA to Isla de Vieques is an approximately 8.5-hour flight. The time zone difference moving from Eastern Standard Time to Atlantic Standard Time is 1 hour. When traveling from Philadelphia in October, plan for a bit warmer days in Isla de Vieques, with highs around 88°F, while nights are warmer with lows around 76°F. Finish your sightseeing early on the 30th (Fri) so you can travel to San Juan.

Things to do in Isla de Vieques

Outdoors · Parks · Beaches · Nature
Find places to stay Oct 28 — 30:
Highlights from your plan
Marauder Sailing Charters - Private Tours ©
Marauder Sailing Charters - Private Tours
Sun Bay Beach ©
Sun Bay Beach
La Chiva ©
La Chiva

3
nights
San Juan, Puerto Rico

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Step out of San Juan with an excursion to El Yunque Rain Forest in El Yunque National Forest--about 1h 10 min away. There's much more to do: get to know the fascinating history of Old San Juan, skim along the rocks with a canyoning and rapelling tour, let your taste buds guide you at a local gastronomic tour, and enjoy the sand and surf at Pine Grove Beach.

For where to stay, more things to do, photos, and more tourist information, read San Juan travel itinerary planner.

You can fly from Isla de Vieques to San Juan in 2 hours. Other options are to do a combination of ferry and car; or do a combination of ferry and shuttle. Expect a daytime high around 90°F in October, and nighttime lows around 78°F. Finish your sightseeing early on the 2nd (Mon) so you can travel to Punta Cana.

Things to do in San Juan

Parks · Outdoors · Nature · Wildlife

Side Trips

Find places to stay Oct 30 — Nov 2:
Highlights from your plan
Canyoning & Rappelling Tours
El Yunque Rain Forest ©
El Yunque Rain Forest
Old San Juan ©
Old San Juan

3
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.
Punta Cana is known for beaches, wildlife, and adventure. Your plan includes some of its best attractions: take an unforgettable tour with Dominicana.pro, enjoy unforgettable views with Dominican Balloons, stroll through Bavaro Beach, and try your luck at Hard Rock Casino Punta Cana.

For photos, other places to visit, where to stay, and tourist information, read Punta Cana trip itinerary planner.

Getting from San Juan to Punta Cana by flight takes about 2.5 hours. Other options: do a combination of ferry and bus. In November, daytime highs in Punta Cana are 85°F, while nighttime lows are 74°F. Finish your sightseeing early on the 5th (Thu) to allow enough time to take a shuttle to Santo Domingo.

Things to do in Punta Cana

Outdoors · Tours · Parks · Wildlife
Find places to stay Nov 2 — 5:
Highlights from your plan
Dominican Balloons ©
Dominican Balloons
Bavaro Beach ©
Bavaro Beach
Punta Espada Golf Course ©
Punta Espada Golf Course

2
nights
Santo Domingo, Dominican Republic

Santo Domingo ©
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
On the 6th (Fri), appreciate the history behind Columbus Lighthouse (Faro A Colon), then see the interesting displays at Museo De Las Casas Reales, then step into the grandiose world of Alcazar de Colon, and finally take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor. Get ready for a full day of sightseeing on the 7th (Sat): don't miss a visit to Zona Colonial.

To find ratings, reviews, traveler tips, and more tourist information, refer to the Santo Domingo trip builder tool.

Getting from Punta Cana to Santo Domingo by shuttle takes about 2 hours. Other options: drive; or fly. Wrap up your sightseeing on the 7th (Sat) early enough to travel to Orlando.

Things to do in Santo Domingo

Find places to stay Nov 5 — 7:
Highlights from your plan
Museo De Las Casas Reales ©
Museo De Las Casas Reales
Zona Colonial ©
Zona Colonial
Alcazar de Colon ©
Alcazar de Colon

5
nights
Orlando, United States

Orlando ©

Theme Park Capital of the World

For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Pack the 9th (Mon) with family-friendly diversions at Universal's Islands of Adventure. Pack the 12th (Thu) with family-friendly diversions at Universal Orlando Resort. The adventure continues: make an unforgettable trip to Walt Disney World Resort, find something for the whole family at SeaWorld, and explore the world behind art at Charles Hosmer Morse Museum of American Art.

For reviews, photos, ratings, and more tourist information, use the Orlando holiday tool.

You can fly from Santo Domingo to Orlando in 7 hours. The time zone difference when traveling from Santo Domingo to Orlando is minus 1 hour. In November, plan for daily highs up to 78°F, and evening lows to 62°F. Finish up your sightseeing early on the 12th (Thu) so you can travel to Tulum.

Things to do in Orlando

Side Trip

Find places to stay Nov 7 — 12:
Highlights from your plan
Magic Kingdom Park ©
Magic Kingdom Park
Universal's Islands of Adventure ©
Universal's Islands of Adventure
Universal Orlando Resort ©
Universal Orlando Resort

4
nights
Tulum, Mexico

Tulum ©
The only Mayan site built to overlook the ocean, Tulum remains a coastal paradise preserving the last vestiges of a pre-Hispanic civilization.
Change things up with a short trip to Xcaret in Playa del Carmen (about 58 minutes away). There's lots more to do: delve into the distant past at Tulum Archaeological Site, explore the activities along Gran Cenote, kick back and relax at Paradise Beach, and take in panoramic vistas at Tulum Tower.

For where to stay, other places to visit, photos, and tourist information, read Tulum trip builder.

Traveling by flight from Orlando to Tulum takes 7 hours. Alternatively, you can drive; or do a combination of bus and car. Traveling from Orlando in November, Tulum is a bit warmer at night with lows of 69°F. Cap off your sightseeing on the 16th (Mon) early enough to travel to Mexico City.

Things to do in Tulum

Outdoors · Parks · Beaches · Theme Parks

Side Trips

Find places to stay Nov 12 — 16:
Highlights from your plan
Xel-Ha Park by Xcaret ©
Xel-Ha Park by Xcaret
Xcaret ©
Xcaret
Tulum Archaeological Site ©
Tulum Archaeological Site

3
nights
Mexico City, Mexico

Mexico City ©

City of Palaces

Breathtakingly large, Mexico City provides a home for almost 9 million people living in nearly 1,700 distinct neighborhoods.
When in Mexico City, make a side trip to see Zona Arqueológica de Teotihuacan Estacionamiento Puerta 5 in San Juan Teotihuacan, approximately San Juan Teotihuacan away. There's much more to do: take an in-depth tour of Museo Nacional de Antropologia, don't miss a visit to Museo Frida Kahlo, delve into the distant past at Museo del Templo Mayor, and admire the masterpieces at Palacio de Bellas Artes.

For ratings, traveler tips, reviews, and more tourist information, read Mexico City driving holiday planning site.

You can fly from Tulum to Mexico City in 6 hours. Other options are to drive; or take a bus. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. Traveling from Tulum in November, you will find days in Mexico City are slightly colder (72°F), and nights are colder (49°F). Finish your sightseeing early on the 19th (Thu) to allow enough time to travel to Las Vegas.

Things to do in Mexico City

Side Trip

Find places to stay Nov 16 — 19:
Highlights from your plan
Museo del Tiempo Tlalpan ©
Museo del Tiempo Tlalpan
Museo Nacional de Antropologia ©
Museo Nacional de Antropologia
Palacio de Bellas Artes ©
Palacio de Bellas Artes

5
nights
Las Vegas, United States

Las Vegas ©

Sin City

Nicknamed the "Entertainment Capital of the World," Las Vegas sits in the middle of a desert in the southern section of Nevada.
When in Las Vegas, make a side trip to see Hoover Dam in Boulder City, approximately Boulder City away. There's much more to do: make a trip to Fountains of Bellagio, see the interesting displays at The Mob Museum, admire the majestic nature at Red Rock Canyon National Conservation Area, and try to win big at Bellagio Hotel and Casino.

For other places to visit, photos, traveler tips, and tourist information, refer to the Las Vegas online itinerary planner.

Fly from Mexico City to Las Vegas in 7.5 hours. Alternatively, you can drive; or do a combination of bus and tram. The time zone changes from Central Standard Time (CST) to Pacific Standard Time (PST), which is usually a -2 hour difference. In November, daytime highs in Las Vegas are 68°F, while nighttime lows are 47°F. Finish your sightseeing early on the 24th (Tue) to allow enough time to travel to Chicago.

Things to do in Las Vegas

Parks · Fun & Games · Casinos · Shopping

Side Trip

Find places to stay Nov 19 — 24:
Highlights from your plan
Fountains of Bellagio ©
Fountains of Bellagio
Red Rock Canyon National Conservation Area ©
Red Rock Canyon National Conservation Area
The Strip ©
The Strip

6
nights
Chicago, United States

Chicago ©

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, and nightlife. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, admire the striking features of Skydeck Chicago - Willis Tower, make a trip to Millennium Park, and contemplate the long history of Ernest Hemingway Birthplace.

For traveler tips, maps, other places to visit, and other tourist information, refer to the Chicago driving holiday planning website.

You can fly from Las Vegas to Chicago in 6 hours. Alternatively, you can drive; or do a combination of bus and train. The time zone difference when traveling from Las Vegas to Chicago is 2 hours. Plan for a bit cooler temperatures traveling from Las Vegas in November, with highs in Chicago at 50°F and lows at 35°F. Finish your sightseeing early on the 30th (Mon) so you can travel to Toronto.

Things to do in Chicago

Museums · Parks · Childrens Museums · Historic Sites

Side Trips

Find places to stay Nov 24 — 30:
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry
Field Museum ©
Field Museum

4
nights
Toronto, Canada

Toronto ©

New York City of Canada

Possibly the world's most diverse city, Toronto houses over 80 ethnic communities speaking nearly 150 different languages or dialects.
Get out of town with these interesting Toronto side-trips: Niagara Falls (Skylon Tower, Niagara Falls Canada, &more). There's lots more to do: admire the striking features of CN Tower, explore the historical opulence of Casa Loma, take in the spiritual surroundings of St Michael's Cathedral Basilica, and see the interesting displays at Hockey Hall of Fame.

To see where to stay, ratings, maps, and other tourist information, read our Toronto online travel route planner.

Traveling by combination of flight and ferry from Chicago to Toronto takes 5 hours. Alternatively, you can drive; or do a combination of train and car. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. In November in Toronto, expect temperatures between 46°F during the day and 35°F at night. Wrap up your sightseeing on the 4th (Fri) early enough to travel to Montreal.

Things to do in Toronto

Side Trip

Find places to stay Nov 30 — Dec 4:
Highlights from your plan
Casa Loma ©
Casa Loma
CN Tower
CN Tower
Royal Ontario Museum ©
Royal Ontario Museum

2
nights
Montreal, Canada

Montreal ©

Quebec's Metropolis

Quebec's economic and cultural capital, Montreal serves as the province's major point of entry, known for its rich history and high standard of living.
Kick off your visit on the 5th (Sat): take in the architecture and atmosphere at Notre-Dame Basilica, then see the interesting displays at Pointe-a-Calliere, Montreal Archaeology and History Complex, and then take in the spiritual surroundings of Saint Joseph's Oratory of Mount Royal. On the next day, pick up some local products at Jean-Talon Market, then take in nature's colorful creations at Montreal Botanical Garden, and then walk around Mount Royal Park.

To find ratings, other places to visit, reviews, and other tourist information, you can read our Montreal travel route website.

Traveling by combination of ferry and flight from Toronto to Montreal takes 4 hours. Alternatively, you can take a train; or drive. Traveling from Toronto in December, expect Montreal to be a bit cooler, temps between 29°F and 20°F. Wrap up your sightseeing on the 6th (Sun) early enough to drive to Quebec City.

Things to do in Montreal

Find places to stay Dec 4 — 6:
Highlights from your plan
Montreal Botanical Garden ©
Montreal Botanical Garden
Notre-Dame Basilica ©
Notre-Dame Basilica

4
nights
Quebec City, Canada

Quebec City ©
With a World Heritage-listed old town, Quebec City remains a walkable and safe hub of culture, commerce, and education offering a blend of fascinating history and a range of tourist-oriented activities.
Quebec City is known for historic sites, nature, and museums. Your plan includes some of its best attractions: get to know the fascinating history of Old Quebec, wander the streets of Terrasse Dufferin, walk around Parc de la Chute-Montmorency, and take in the spiritual surroundings of Eglise Notre Dame des Victoires.

To see maps, other places to visit, ratings, and more tourist information, use the Quebec City driving holiday tool.

Traveling by car from Montreal to Quebec City takes 3 hours. Alternatively, you can take a bus; or take a train. Finish your sightseeing early on the 10th (Thu) to allow enough time to travel to New York City.

Things to do in Quebec City

Historic Sites · Neighborhoods · Parks · Museums
Find places to stay Dec 6 — 10:
Highlights from your plan
Old Quebec ©
Old Quebec
Parc de la Chute-Montmorency ©
Parc de la Chute-Montmorency
The Battlefields Park ©
The Battlefields Park

6
nights
New York City, United States

New York City ©

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
New York City is known for museums, nightlife, and shopping. Your plan includes some of its best attractions: go for a walk through Central Park, make a trip to Rockefeller Center, appreciate the history behind Statue of Liberty National Monument, and explore the galleries of 9/11 Memorial.

For more things to do, reviews, maps, and more tourist information, read our New York City trip planning website.

Traveling by flight from Quebec City to New York City takes 6 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 48°F in December, and nighttime lows around 36°F. Finish your sightseeing early on the 16th (Wed) to allow enough time to take a train back home.

Things to do in New York City

Find places to stay Dec 10 — 16:
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

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