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Boston - Cape Cod - New York (Self Drive)
7 to 11+ nights from $1,293*Explore Massachusetts and New York as you enjoy some of its most iconic cities. Combine Boston (the capital Massachusetts; home of the Boston Red Soxs and New England Patriots), Cape Cod and New York (the capital of the world,' very famous for its diverse entertainment venues, gastronomy and nightlife). Travel through the cities with a r ...
Boston - Cape Cod - New York (Self Drive)
7 to 11+ nights from $1,293 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-27T00:00:00. Choose your own departure city and dates.
This 7 night sample itinerary includes:
- Flight into Boston and out of New York City
- Rental Car for 5 days
- Pick up last day in Boston and drop off first day in New York
- Hotel for 2 nights in Boston
- Hotel for 2 nights in Cape Cod
- Hotel for 3 nights in New York
Driving Time
Boston – Cape Cod: 1 hr 27 min approx.
Cape Cod- New York: 4 hr 36 min approx
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Boston - Kennebunkport - Bar Harbor - Bangor (Self Drive)
6 to 9+ nights from $1,542*Rolling green hills, beautiful panoramic views of the sea, and thrilling's cities you will discover with this Self-Drive package across Massachusetts and Maine States. Start in Boston (one of the oldest and populous cities of Massachusetts, famous for its baked beans and the Boston Marathon). After that, drive up to Maine Coast and spend ...
Boston - Kennebunkport - Bar Harbor - Bangor (Self Drive)
6 to 9+ nights from $1,542 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-18T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Boston and out of Bangor
- Hotel for 2 nights in Boston
- Rental Car for 5 days
- Hotel for 1 night in Kennebunkport
- Hotel for 2 nights in Bar Harbor
- Hotel for 1 night in Bangor
Driving Time
Boston - Kennebunkport: 1 hrs. 35 min. approx.
Kennebunkport - Bar Harbor: 3 hrs. 30 mins approx.
Bar Harbor - Bangor: 1 hr. 10 mins approx.
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Massachusetts and Maine Coastal (Self-Drive)
10 to 15+ nights from $2,219*Enjoy this Road Trip to The Bay and The Pine Tree States; with their charming coastal towns. Make sure you are hungry, as you will be find many delicious lobster dishes throughout the trip. Start in Massachusetts, visiting Boston (historic city and capital of Massachusetts famous for the Boston Tea Party); then, drive to Maine State and e ...
Massachusetts and Maine Coastal (Self-Drive)
10 to 15+ nights from $2,219 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-26T00:00:00. Choose your own departure city and dates.
This 10 night sample itinerary includes:
- Flight into Boston and out of Bangor
- Hotel for 3 nights in Boston
- Rental Car for 8 days
- Hotel for 2 nights in Kennebunkport
- Hotel for 1 night in Boothbay Harbor
- Hotel for 3 nights in Bar Harbor
- Hotel for 1 night in Bangor
Driving Time
Boston - Kennebunkport: 1 hr. 35 mins. approx.
Kennebunkport - Boothbay Harbor: 1 hr. 45 mins. approx.
Boothbay Harbor - Bar Harbor: 2 hrs. 50 mins. approx.
Bar Harbor - Bangor: 1 hr. 15 mins. approx.
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Boston and Providence Getaway by Train
5 to 7+ nights from $726*Beautiful panoramic views of the sea, and trilling’s cities you will discover with this unique package across Massachusetts and Rhode Island. Start in Boston (one of the oldest and populous cities of Massachusetts, famous for its baked beans and the Boston Marathon). After that, take a train to Providence (situated at the mouth of the Pr ...
Boston and Providence Getaway by Train
5 to 7+ nights from $726 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-25T00:00:00. Choose your own departure city and dates.
This 5 night sample itinerary includes:
- Flight into Boston and out of Providence
- Hotel for 3 nights in Boston
- Train from Boston to Providence
- Hotel for 2 nights in Providence
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Boston and Washington DC by Air
6 to 9+ nights from $833*Get ready for an epic trip to the heart of Massachussets and DC!, Come have an amazing time in one of the oldest and coolest cities in Massachusetts, Boston (home of the Boston Red Soxs and New England Patriots and famous for the Boston Tea Party) and after that, take a flight to the capital of the US and a prominent political hub worldwi ...
Boston and Washington DC by Air
6 to 9+ nights from $833 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-25T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Boston and out of Washington DC
- Hotel for 3 nights in Boston
- Flight from Boston to Washington DC
- Hotel for 3 nights in Washington DC
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The Best Boston Getaway
4 to 6+ nights from $923*Explore the highlights of the heart of Massachusetts. This package offers Guided tours to famous Freedom Trail, a Harbor Cruise and the North End Food along Boston (one of the oldest and populous cities of Massachusetts, famous for its baked beans, Boston Marathon and tea party). What Makes Tripmasters Vacation Packages Different?Unique, ...
The Best Boston Getaway
4 to 6+ nights from $923 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-09-25T00:00:00. Choose your own departure city and dates.
This 4 night sample itinerary includes:
- Flight into and out of Boston
- Hotel for 4 nights in Boston
Sample of Included Tours: - Freedom Trail Walking Experience in Boston
- Guided North End Food Tour in Boston
Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.
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Washington DC and Boston by Air
6 to 9+ nights from $959*DC and Massachusetts` capitals!. Visit the iconic US capital and political center of the world, Washington DC (a cultural center for its history, national monuments, famous museums and local flavors) and after that, catch a flight to one of the oldest and popular cities of Massachusetts, Boston (home of the Boston Red Soxs and New Englan ...
Washington DC and Boston by Air
6 to 9+ nights from $959 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-09T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into Washington DC and out of Boston
- Hotel for 3 nights in Washington DC
- Flight from Washington DC to Boston
- Hotel for 3 nights in Boston
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Boston and Portland Getaway by Train
5 to 7+ nights from $997*Grab your tickets, sit back, and get ready for an amazing adventure in these cities of Massachusetts and Maine!. Experience the stunning scenery of Boston (home of the Boston Red Soxs and New England Patriots and famous for the Boston Tea Party) and Portland (port city, best known for its marine industry, appreciation for the arts, it’s ...
Boston and Portland Getaway by Train
5 to 7+ nights from $997 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-21T00:00:00. Choose your own departure city and dates.
This 5 night sample itinerary includes:
- Flight into Boston and out of Portland
- Hotel for 3 nights in Boston
- Flight from Boston to Portland
- Hotel for 2 nights in Portland
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Historic Boston Getaway
4 to 6+ nights from $1,044*Massachusetts` Capital!. Revolution, taxes, ghosts, immigration, seafood... It's all part of the history that makes Boston (home of the Boston Red Soxs and New England Patriots and famous for Tea Party) so unique. With this Tour, you'll focus on the famous Freedom Trail. You will also get to taste delicious food (which has been a major co ...
Historic Boston Getaway
4 to 6+ nights from $1,044 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-08-01T00:00:00. Choose your own departure city and dates.
This 4 night sample itinerary includes:
- Flight into and out of Boston
- Hotel for 4 nights in Boston
Sample of Included Tours: - Freedom Trail Walking Experience
- Beyond the Trail City Adventure
- Ghosts Tour Adventure
- Guided North End Food Tour
Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.
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Washington DC - New York City - Boston by Air
7 to 11+ nights from $1,068*Experience historic and lively Washington DC (a political and cultural powerhouse) with a stroll around the National Mall to visit its iconic landmarks and museums, or get a feel for the city`s vibrant arts scene and youthful ambiance. Then, spend a few exciting days in New York City (a cosmopolitan city full of entertainment, beautiful s ...
Washington DC - New York City - Boston by Air
7 to 11+ nights from $1,068 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-18T00:00:00. Choose your own departure city and dates.
This 7 night sample itinerary includes:
- Flight into Washington DC and out of Boston
- Hotel for 2 nights in Washington DC
- Flight from Washington DC to New York City
- Hotel for 3 nights in New York City
- Flight from New York City to Boston
- Hotel for 2 nights in Boston
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New York City and Boston for Outdoor Enthusiasts
6 to 9+ nights from $1,077*New York and Massachusetts favorite cities to enjoy outdoors!. Bike through Central Park and see the epic skylines of New York City (one of the world's largest entertainment and culture capitals, with stunning urban views) and Boston (home of the Boston Red Soxs and New England Patriots) by boat. If you want to do more than just meander ...
New York City and Boston for Outdoor Enthusiasts
6 to 9+ nights from $1,077 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-17T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into New York City and out of Boston
- Hotel for 3 nights in New York City
- Flight from New York City to Boston
- Hotel for 3 nights in Boston
Sample of Included Tours: - Central Park Guided Bike Tour in New York City
- Sightseeing Cruise Experience in New York City
- Freedom Trail Walking Experience in Boston
- Harbor Cruise Experience in Boston
Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.
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Historic New York City and Boston
6 to 9+ nights from $1,186*Prepare yourself as the weight of history embraces you in main cities of New York and Massachussets State. Indulge in the captivating historical narratives of New York City (one of the world's largest entertainment and culture capitals with stunning urban views) and Boston (home of the Boston Red Soxs and New England Patriots and famous f ...
Historic New York City and Boston
6 to 9+ nights from $1,186 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-28T00:00:00. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into New York City and out of Boston
- Hotel for 3 nights in New York City
- Flight from New York City to Boston
- Hotel for 3 nights in Boston
Sample of Included Tours: - 911 Memorial and Statue of Liberty Combo in New York City
- Gilded Age Mansions Tour in New York City
- Freedom Trail Walking Experience in Boston
- Beyond the Trail City Adventure in Boston
- Ghosts Tour Adventure in Boston
Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.
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Boston and Washington DC Getaway by Train
5 to 7+ nights from $1,222*Get ready for an epic trip to the heart of Massachussets and DC!, Come have an amazing time in one of the oldest and coolest cities in Massachusetts, Boston (home of the Boston Red Soxs and New England Patriots and famous for the Boston Tea Party) and after that, take a train to the capital of the US and a prominent political hub worldwid ...
Boston and Washington DC Getaway by Train
5 to 7+ nights from $1,222 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-15T00:00:00. Choose your own departure city and dates.
This 5 night sample itinerary includes:
- Flight into Boston and out of Washington
- Hotel for 2 nights in Boston
- Train from Boston to Washington DC
- Hotel for 3 nights in Washington DC
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Salem and The Berkshires (Self Drive)
5 to 7+ nights from $1,239*Explore Massachusetts, a popular option for more experienced travelers, those looking to get off the beaten path and take their own time with a rental car. Combine Boston (One of the oldest and populous cities of Massachusetts, famous for its baked beans and the Boston Marathon), Salem and The Berkshires (A popular vacation destination, ...
Salem and The Berkshires (Self Drive)
5 to 7+ nights from $1,239 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-08-01T00:00:00. Choose your own departure city and dates.
This 5 night sample itinerary includes:
- Flight into Boston and out of Albany
- Rental Car for 6 days
- Hotel for 1 nights in Boston
- Hotel for 2 nights in Salem
- Hotel for 2 nights in The Berkshires
Driving Time
Boston - Salem: 38 min. approx.
Salem - The Berkshires: 2 hr 32 mins approx. .
The Berkshires - Albany Airport: 1 hr 2 mins approx.
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Fall Foliage Escape (Boston - White Mountains National Park - Portland - Portsmouth - Self Drive)
7 to 11+ nights from $1,269*Take Massachusetts, New Hampshire and Maine into your own hands, travelling between this popular cities with a rental car. Visit Boston (Historic city and capital of Massachusetts famous for the Boston Tea Party), White Mountains National Park, Portland and Portsmouth (Nestled near the mouth of the Piscataqua River, known for the waterfr ...
Fall Foliage Escape (Boston - White Mountains National Park - Portland - Portsmouth - Self Drive)
7 to 11+ nights from $1,269 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-08-16T00:00:00. Choose your own departure city and dates.
This 7 night sample itinerary includes:
- Flight into and out of Boston
- Rental Car for 7 days
- Hotel for 2 nights in Boston
- Hotel for 2 nights in White Mountains National Park
- Hotel for 1 night in Portland
- Hotel for 1 night in Portsmouth
- Hotel for 1 night in Boston
Driving Time
Boston – White Mountain National Park: 2hrs approx.
White Mountain National Park - Portland: 2 hr 30 mins approx.
Portland - Portsmouth: 54 mins approx.
Portsmouth - Boston: 1 hrs 7 mins approx.
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The Best of Washington DC and Boston
7 to 11+ nights from $1,271*Explore the wonders of Washington DC (distinguished by its rich historical heritage, iconic national landmarks, esteemed museums, and delightful local culinary offerings) and Boston (Massachusetts capital state, home of the Boston Red Soxs and New England Patriots and famous for the Boston Tea Party). Visit their main monuments, Capitol H ...
The Best of Washington DC and Boston
7 to 11+ nights from $1,271 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-17T00:00:00. Choose your own departure city and dates.
This 7 night sample itinerary includes:
- Flight into Washington DC and out of Boston
- Hotel for 4 nights in Washington DC
- Flight from Washington DC and Boston
- Hotel for 3 nights in Boston
Sample of Included Tours: - Guided Highlights and Monuments Tour In Washington DC
- Guided Capitol Hill Tour In Washington DC
- Food Tour Experience In Washington DC
- Freedom Trail Walking Experience in Boston
- Ghosts Tour Adventure in Boston
- Guided North End Food Tour in Boston
Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.
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Historic Washington DC and Boston
7 to 11+ nights from $1,278*Perhaps no other two cities in the USA are so emblematic of our history and the vision of our founding fathers than Washington DC (rich historical heritage, iconic national landmarks and esteemed museums) and Boston (considered by many to be the birthplace of the American Revolution). Relive The Freedom Trail, learn about the ghosts of ou ...
Historic Washington DC and Boston
7 to 11+ nights from $1,278 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-28T00:00:00. Choose your own departure city and dates.
This 7 night sample itinerary includes:
- Flight into Washington DC and out of Boston
- Hotel for 4 nights in Washington DC
- Flight from Washington DC to Boston
- Hotel for 3 nights in Boston
Sample of Included Tours: - Guided Capitol Hill Tour In Washington DC
- Guided Night Tour In Washington DC
- Day Trip Alexandria and Mt Vernon from Washington DC
- National Mall Adventure In Washington DC
- Freedom Trail Walking Experience in Boston
- Beyond the Trail City Adventure in Boston
- Ghosts Tour Adventure in Boston
Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.
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Washington DC and Boston Getaway by Train
5 to 7+ nights from $1,304*Capture the essence of pure beauty of DC and Massachusetts main cities!. Visit the capital of the US and a prominent political hub worldwide, Washington DC (distinguished by its rich historical heritage, iconic national landmarks, esteemed museums, and delightful local culinary offerings) and after that, come aboard the train and embark t ...
Washington DC and Boston Getaway by Train
5 to 7+ nights from $1,304 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-20T00:00:00. Choose your own departure city and dates.
This 5 night sample itinerary includes:
- Flight into Washington DC and out of Boston
- Hotel for 3 nights in Washington DC
- Train from Washington DC to Boston
- Hotel for 2 nights in Boston
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Gloucester - Kennebunkport - Concord NH - Boston (Self Drive)
7 to 11+ nights from $1,338*These New England' States; Massachusetts, Maine New Hampshire are combined in this Self-Drive Package for an unforgettable holiday. Start in Gloucester (worth visiting for its history, seafood restaurants, whale watch cruises, artists' colony, historic houses, and its fine beaches). Then drive up to the southern Maine coastal area, to Ken ...
Gloucester - Kennebunkport - Concord NH - Boston (Self Drive)
7 to 11+ nights from $1,338 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-21T00:00:00. Choose your own departure city and dates.
This 7 night sample itinerary includes:
- Flight into and out of Boston
- Rental Car for 6 days
- Hotel for 2 nights in Gloucester
- Hotel for 2 nights in Kennebunkport
- Hotel for 1 night in Concord NH
- Hotel for 2 nights in Boston
Driving Time
Boston Airport - Gloucester: 55 min. approx.
Gloucester - Kennebunkport: 1 hr. 40 mins approx.
Kennebunkport - Concord NH: 1 hr. 30 mins approx.
Concord NH - Boston: 1 hr. 10 mins. approx.
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Washington DC - New York City - Boston by Train
8 to 12+ nights from $1,412*Embark on a magnificent journey aboard a mesmerizing train, discovering main cities in Washington, the DC and Massachusetts States!. Visit: Washington DC (distinguished by its rich historical heritage, iconic national landmarks, esteemed museums, and delightful local culinary offerings), after that, New York City (one of the world's large ...
Washington DC - New York City - Boston by Train
8 to 12+ nights from $1,412 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-07-17T00:00:00. Choose your own departure city and dates.
This 8 night sample itinerary includes:
- Flight into Washington DC and out of Boston
- Hotel for 3 nights in Washington DC
- Train from Washington DC to New York City
- Hotel for 3 nights in New York City
- Train from New York City to Boston
- Hotel for 2 nights in Boston