About Cheers to Boston Weekend

Whether you’re in town for a cold one at Cheers, shopping Newbury Street or reliving history on the Freedom Trail, the fun and interest never end in Boston, home of the Red Sox and Celtics. One if by land, two if by sea, if you are single, it’s where you want to be!

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Inclusive Features of our Tour:

  • 3 Nights, Peak Season, Accommodations at newly renovated Boston Park Plaza, located in the heart of Boston, within walking distance of most major sites.
  • Welcome Lobster Bake Dinner at Legal Sea Foods & Glass of Prosecco
  • Complimentary Internet at the Park Plaza
  • Freedom Trail Walking Tour Narrated by a Famous Historic Character.
  • Dim Sum lunch in Chinatown on Saturday followed by Sam Adams Brewery Tour & Tasting
  • Farewell Dinner at the Original Cheers with 2 Course Dinner and 1 Drink: Join more singles cruising with us tomorrow, who just arrived.
  • OPTIONAL: Saturday Night Party at Faneuil Hall or Historic Boston Pub Crawl (drinks and meals at own expense)
  • OPTIONAL: Sunday Touring Choices – New England Aquarium with Whale Watching, USS Constitution Museum, Bunker Hill Monument, Shopping Newbury Street & More!
  • Hotel Taxes-15%


  • Experienced, Professional STI Travel Concierge
  • Free Roommate Matching
  • Company of Other Fun Loving Singles while in Boston
  • Private Online Chat Accessible to Members on the Tour; Meet and Plan Before you Go, So MUCH to do!

Inclusive features are subject to revision at the discretion of STI and our local operators. Ages listed are not meant as a restriction, but are simply used as a guideline. Singles Travel International does not guarantee the number of guests, ages or ratios.

NOTE: Our weekend package includes features that are mainly within walking distance; Boston is a walking city. Come prepared with comfortable shoes and at any time, you are welcome to take a taxi at your own expense.


Tour Begins in Boston: September 1, 2017
Tour Ends in Boston: September 4, 2017

Day 1 – Friday – September 1

Flights arrive into Boston and transfer on your own to the Boston Park Plaza Hotel in the heart of Boston, within walking distance of almost every major site.

Check-in with our Singles Travel International Concierge upon arrival at the hotel. Need help with sightseeing, shopping and dinner reservations? We’re here to make sure your vacation is everything you dreamt it would be!

This evening, we kick off the weekend with a Lobster Bake at Legal Sea Foods. ‘If it isn’t fresh, it isn’t Legal’ is the slogan at this popular chain – stretching from Florida to Massachusetts – which has its own waterfront purity lab that inspects every delivery. Famed for its thick and bipartisan New England clam chowder, which has been served at the Presidential Inaugurations of all five presidents since Ronald Reagan in 1981, it also has a huge menu of every sorts of seafood dish.” – USA Today. Enjoy a 3-course dinner of clam chowder, steamers, mussels, chouriço, corn on the cob and a 1.25 lb. lobster with your fellow travelers. Meet many of our local, Boston members who came out to greet you. One drink, tax, gratuity, coffee and tea are included. A cash bar is available for additional drinks or wine with dinner.

After dinner, we head back to the hotel for a nightcap or rely on our locals to show us the town!

Day 2 – Saturday – September 2

Good morning! Breakfast is optional, but we’ve got some great recommendations.

This morning, we step back in history as we walk the Freedom Trail in the footsteps of a famous figure in history. Who will that be? The 2.5 mile red line leads to nationally significant historic sites, each one an authentic treasure. Preserved and dedicated by the citizens of Boston in 1951, the Freedom Trail is a unique collection of museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers that tell the story of the American Revolution and beyond. Click here to see the official sites on the Trail. We won’t see them all on our tour, but you have time to explore with new friends this afternoon based on your own personal interests.

Meet up near Haymarket for an Oyster & Chowder lunch at Union Oyster House, recently named the 5th Best Seafood restaurant in the USA. Lunch is at your own expense. Oysters not your cup of tea (pun intended), there are plenty of nearby restaurants from which to choose.

Anyone up for a Boston Duck experience this afternoon? Great fun for a group (optional). Click to book now.

Our evening is at leisure and STI has 2 fun recommendations. Option 1: Faneuil Hall Happy Hour and Dinners at one of many alternatives. Option 2: Historic Pub Crawl with Bar Snack Dinner.  All events are at your own expense and we ask that you select your choice at time of booking. Whatever your pleasure, our Singles Travel International Concierge is available to assist with making plans.

Day 3 – Sunday – September 3

Breakfast is at leisure, grab a small bite nearby, and hit the sites,

This morning, you are free to enjoy Boston and all it has to offer. Maybe you are a history buff and more Freedom Trail, USS Constitution or Bunker Hill are your idea of fun. Nature lovers will enjoy the New England Aquarium with Whale Watching experience or a walk in the park (Boston Commons) to enjoy the gardens and fall foliage. Foodies, join us for a Dim Sum lunch in Chinatown, followed by a short train ride to the Sam Adams Brewery for a tour and tasting. Lunch and Tour are included in our package.

Tonight, we gather at the hotel before our 10 minute walk to the Original Cheers from the famous American sitcom that ran for eleven seasons between 1982 and 1993. At STI, we always know your name.

Dinner is a 2 course, casual event including 1 drink to get us all together for some good fun and cheer before we go home or head out on the cruise.

Now that you know the “lay of the land, 2 if by sea” of this great city, make the most of your Sunday night with new friends.

Day 4 – Monday – September 4

Breakfast is at leisure.

Check out at noon and transfer to the airport for our flights home.

Our weekend in Boston is a walking weekend. In other words, all of our activities are within walking distance of our hotel (6-8 blocks or closer). If you require transportation, we will gladly assist at your own expense.


Once you make your online reservation, an STI reservation specialist will contact you to review and recommend additional services. Depend on them for assistance with airfare, proper protection, pre and post tour services. Once that step is complete, you will receive a final invoice from us confirming your reservation details.

READ your invoice and the FAQ page very carefully and advise if any changes need to be made.

Next, say hello to your fellow travelers on the chat!

Click Here! for your “Final Vacation Details & Meetup Information” including transportation and how to meet up with the group. Questions? Email us at service@singlestravelintl.com.

The tour begins in Boston at 3:00 p.m. on Friday, September 1, 2017 and ends in Boston on Monday morning, September 4, 2016. Therefore the trip is 3 nights/4 days.

To make the most of your weekend, we recommend that you arrive at the Boston Park Plaza Hotel, 50 Park Plaza at Arlington Street, Boston, MA 02116, 800-225-2008, by 3:00 p.m. on Friday. Note that check-in is at 3:00 p.m. In the event that you arrive early, the bell desk will gladly hold your bags while you’re out on the town.

Our STI Concierge will be at our hospitality desk this afternoon to meet and greet you followed by our first event, Lobster Bake dinner at approximately 7:00 p.m. You won’t want to miss it!

A deposit is due at time of reservation. Refer to the Price and Options tab for the amount. Final payment is due in our office by June 2, 2017. A reminder will be emailed to you 7 days prior to due date and your card will automatically be charged. If you make a reservation after June 2, full payment will be automatically charged at time of reservation and penalties will apply.

Yes. All cancellations must be made in writing to Singles Travel International and are subject to per person penalties as follows:

After deposit and at anytime of cancellation, a minimum charge of $75.00 plus credit card charges will apply in addition to other penalties listed below.

Between June 2 and August 2, 2017 – $300 penalty applies.
After August 2, 2017 – 100% penalty applies.

Note that if you elect to take a roommate and he/she cancels after our cut off date, we will do everything to find a new match. However, if no match is found, the difference in cost for a single cabin/room is the responsibility of the guest who cancels. No refund will be given to the guest who cancels, regardless of cruise or tour company policy as stated above. Singles Travel International is not responsible for costs related to cancellations after our cut off date.

In order to accommodate singles from all over the world, our tours and cruises are priced as land only. Therefore, airfare is additional. Singles Travel International is a licensed ticketing agency and oftentimes has low negotiated fares.

Arrive by 3:00 p.m. on Friday, September 1 and depart any time on Monday, September 4, 2017.

From Logan Airport – You have 3 options when arriving at Logan International Airport:

  • Airport Cab Service – 20 minute ride, meter rate, approximately $25 – $45 each way.
  • Boston ‘s Subway ($2.65 each way): The “T”- The Boston Park Plaza Hotel is located on Arlington Stop (Green Line) and Back Bay Stop (Orange Line) – The Hotel is 1 block from the Arlington T Stop off of the Green Line and 3 blocks from the Back Bay T Stop off of the Orange line. Click here for more information.
  • Take a shared shuttle for $24 each way. Click here to book.

Parking at the hotel is $51 per night for valet and $32 for self parking across the street at the Motor Mart Garage for $32 per night and is open 24 hours. Rates are subject to change at any time.

Our tour does not include airfare, airport transfers, breakfast, one dinner and two lunches. You are responsible for alcoholic beverages (except when included in STI events), incidentals such as laundry and phone calls, plus gratuities to STI staff ($10-$15 per day) and local guides. Our weekend in Boston is a walking weekend. In other words, all of our activities are within walking distance (6-8 blocks or closer). If you require transportation, we will gladly assist at your own expense.

Absolutely. Our site is so popular that we guarantee to find a roommate for you or the single room is on us! In order to take advantage of our offer, you must be paid in full by June 2, 2017. Of course, single accommodations are available at an additional rate.

Please contact your preferred carrier directly to make your reservation. If Singles Travel International issues a promotional economy fare, granting of frequent flyer credit is entirely at the airline’s discretion. If the flights are eligible, to ensure you earn frequent flyer credit from the airline, give your frequent flyer account number when you check in for your flights. In addition, save your boarding passes and the passenger receipt from your airline ticket. You may need to submit these to the airline (not to Singles Travel International) to claim any credit allowed.

The Boston Park Plaza Hotel, Our luxury, Boston Hotel is close to many Boston Attractions and ‘Things to do in Boston’ including; Boston Shopping on Newbury Street, Faneuil Hall Marketplace, the Theatre & Financial Districts, and many inspirational Boston Landmarks and Boston’s Historical Monuments.

Plus, your STI staff will be on hand to take care of your every need. It’s not only what we do, it’s who we are!

Of course not. You will be pleased to find out that nearly 90% of our guests on every trip sign up and have never met anyone before joining the group. In 24 years, we have perfected the singles vacation experience. It is paramount that our guests meet each other right away and have opportunities to mingle every day. From the moment you join our tour, our STI Concierge is waiting to meet you. Our first day begins with a get together and the camaraderie builds as we go along.

Our “All Ages” vacations cater to 40+ and our average age range is 45-65. We generally have a ratio of 60/40, women to men. Ages listed on our page are not restricted. They are simply used as a guideline. As a travel club, matchmaking is not our focus. We offer an opportunity for single travelers to see the world in the company of other singles and do not guarantee the ratio or ages.

Take advantage of our community features, send individual messages and post to friends and fellow travelers on the chat, exclusively for members on your same tour.

Autumn in Boston is like none other. Expect daytime high temperatures to be in the mid 70s with beautiful changing colors (subject to Mother Nature). Evening temperatures are generally in the mid 60s. Rain is always possible, so come prepared with raingear.

There is no baggage limit at the hotel.

Currently, most airlines will allow you to check up to two bags, weighing 50 pounds each, for a fee. In addition you may carry-on one bag plus a personal item such as a purse or briefcase. Please check with your air carrier for up-to-the minute regulations and fees for checked baggage.

Since temperatures are slightly cooler, fall clothing is best. Remember to bring comfortable shoes and a jacket for evenings. Casual attire is acceptable throughout the weekend. However, you may want to bring something dressy for Thursday night at Legal Sea Foods. Jackets for gentleman are not required.

Packing Tips: Take only what you need; don`t over pack. Save room for souvenirs and purchases. Pack flat and full to avoid wrinkling. Bring wardrobe basics; mix and match around one or two colors. Don`t pack anything valuable, fragile or perishable. Label your luggage with an outside tag, and place an identification card inside each suitcase.

Essential Items: We highly recommend that you bring the following items.

– A great attitude and an open mind.
– A good, comfortable pair of broken-in walking shoes.
– A pair of shoes for restaurants (loafers, sandals, etc).
– Collapsible umbrella (which can double as a sunshade parasol) and/or lightweight raingear.
– Ladies may wish to bring an evening wrap and gentlemen a nicer jacket for evening wear.
– Sweater or k=light jacket.
– Jeans
– Sunglasses, sun block, sun hat or visor.
– Toiletries: all your daily essentials.
– Prescription medications: sufficient supply for the entire trip plus legible written prescription in case of loss. Keep medications in their original, labeled container. Always pack your medications in your carry-on bag!
– Eyeglasses, contacts, contact lens solution. You may want to bring along a written prescription for your eyewear in case of loss.
– Over the counter medications: cold remedy, aspirin/pain reliever, antacid/stomach upset remedy, Band-Aids, anti-bacterial medication.
– Travel alarm clock with illuminated face.
– Small, Swiss Army type utility knife, great for opening wine, packages etc. Remember to pack this in your checked luggage!
– Travel journal/notepad and reading material.
– Home address book for sending postcards. A useful tip to avoid bringing your entire address book is to pre-write names and addresses of people to whom you want to send postcards on sheets of self-adhesive labels. It saves time and space in your luggage.
– Small, basic sewing kit with a few extra buttons. Remember to pack scissors in your checked bag!
– Photography Equipment: Bring a sufficient supply of film and extra batteries.

Travel Insurance is available through Travel Guard and in addition to direct access immediately upon completing your purchase, you will receive a quote from Travel Guard regarding travel insurance after reserving your vacation. If you have any questions, Travel Guard professional, expert agents are available 24 hours a day, 7 days a week. You may also call Singles Travel International if you have not received your quote within 3 days.

Your Final Vacation Details & Meetup Info Documents will be available here on FAQ (question #1), 14 days prior to departure and will include phone contact numbers for each hotel listed in your daily itinerary. We suggest you leave a copy of this with your family.

Our office is open Monday-Friday from 9:00 a.m. to 6:00 p.m. Eastern Standard Time. In an emergency after hours, please contact Tammy Weiler at 815-715-6998.


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Meet Your STI Concierge


I am a compassionate soul who enjoys making others smile. I spend the majority of my free time dancing, meditating, and practicing yoga. When I am not exercising, I love to cook, garden, and spend time with my family and friends. I fluently speak Spanish and love all aspects of the associated cultures.

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What Our Members Are Saying

The trip was a lot of fun. Chicago is very big and interesting. The highlight of the trip had to be our STI Concierge, Mary Delia. She is amazing as a travel guide and should have her own travel TV show. She entertained us and kept us on track for the entire weekend. Everything was outstanding and everyone seemed content.

Fotolia_58389435_Subscription_Monthly_M_04    George A, Newport News, VA

I will have to admit that initially I had some trepidations as to what to expect. But all that dissolved and melted away ( or should I say blown away!). Thank you so much for all the little extra "hoop-la" about Danielle's birthday---it made it very "special" for her. I am already checking out your new list of trips---- most of all saving my $$$$ so that I can do this again & again. Once again, thank you for such a wonderful and fun trip !

Fotolia_58389435_Subscription_Monthly_M_04    Jeroline C, University Park, IL