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BearCruise 15th Anniversary

2027 Boston to San Juan, Puerto Rico

October 20 – 28, 2027

On the Celebrity Summit


ON THE CELEBRITY SUMMIT

Our BearCruisers Depart for a 9-Night Transition Cruise Getaway!

Celebrate 15 Years of BearCruise with an unforgettable journey!  Our first BearCruise was a transition cruise on the Celebrity Summit from Cape Liberty to San Juan.  We think it is a great time to do another transition cruise on the Celebrity Summit to celebrate!

Join BearCruise.com aboard the Celebrity Summit for our 15th Anniversary Cruise, sailing October 20–29, 2027, from Boston to San Juan, Puerto Rico. This spectacular voyage blends vibrant culture, tropical beauty, and community spirit as we explore:

Boston • Puerto Plata • Samana • St. Thomas • Antigua • Tortola • San Juan

From the historic charm of Boston to the colorful streets of Old San Juan, each port offers its own unique flavor. Whether you’re soaking up the sun in the Dominican Republic, snorkeling in the Virgin Islands, or hiking the rainforest in Tortola, this cruise promises connection, celebration, and adventure.

Don’t miss this milestone sailing—where friendship meets paradise.

Itinerary

      • Day 1 – Wednesday, October 20 – Boston – Departs  4 pm
      • Day 2 – Thursday, October 21 – Sailing 
      • Day 3 – Friday, October 22 –  Sailing 
      • Day 4 – Saturday, October 23 – Sailing
      • Day 5 – Sunday, October 24 – Puerto Plata, Dominican Republic – 8 am – 5 pm
      • Day 6 – Monday, October 25 – Samana, Dominican Republic – 7 am – 3 pm
      • Day 7 – Tuesday, October 26 – Charlotte Amalie, St. Thomas – 10 am – 6 pm
      • Day 8 – Wednesday, October 27 – St. Johns, Antiguga – 8 am – 5 pm
      • Day 9 – Thursday, October 28 – Tortola, British Virgin Islands – 8 am – 5 pm
      • Day 10 – Friday, October 29 – San Juan, Puerto Rico – Arrive at 5 am

Your Daily Agenda:

Day 1: Wednesday, October 20, August 5 - Boston- Departs at 4 pm

We recommend a day or two in Boston before we sail. A visit to Boston offers a rich mix of American history, waterfront beauty, and world‑class art. Travelers can begin in the historic North End at the iconic Old North Church, famous for its “one if by land, two if by sea” signal that helped spark the American Revolution. From there, it’s an easy stroll to the lively Faneuil Hall Marketplace and the scenic harborfront. Visitors can explore the city’s revolutionary past at the Boston Tea Party Ships & Museum, then head to the Back Bay to wander the enchanting Isabella Stewart Gardner Museum, a Venetian‑style palace filled with art, flowers, and one of the most intriguing unsolved art heists in history . For a final panoramic view, View Boston offers sweeping city vistas to cap off the day.

Day 2: Thursday, October 21 - Sailing Day

The first full day is a great day to get to know the other BearCruise sailors on board. Whether you are meeting for the first time or renewing old friendships, BearCruise will have activities and meet-ups for you to enjoy with the rest of the group.

Activities like Hot Tub Takeover, the therapy pool in the Solarium, cocktail hour at the Martini Bar, and dinner in the Cosmopolitan Dining Room are on the agenda.

Day 3: Friday, October 22 - Sailing Day

A sea day aboard the Celebrity Summit is all about unwinding and indulging at your own pace. Guests can stretch out by the sparkling pool deck, relax in the tranquil adults‑only Solarium, or enjoy a soothing treatment in the full‑service spa. Culinary lovers can savor long, leisurely meals or join cooking, mixology, or wine‑tasting experiences. Throughout the ship, live music drifts from lounges, trivia and enrichment programs keep the day lively, and the Rooftop Terrace offers a perfect spot to read, nap, or simply watch the ocean roll by. As evening arrives, passengers can enjoy a Broadway‑style show in the theater, sip cocktails at the Martini Bar, or dance under the stars—making a sea day feel every bit as memorable as a day in port.

Day 4:: Saturday, October 23 - Day at Sea

Now you are really starting to get into the swint of this relaxation thing!  Enjoy another awesome day at sea with your best Bearcruise buddies.

Day 5: Sunday, October 24 - Puerto Plata, Domnnican Republic - 8 am - 5 pm

Land ho!!!  We arrive in our first port in the Dominican Republic. 

Cruise passengers spending a day in Puerto Plata can enjoy a vibrant mix of history, scenery, and Caribbean relaxation. Many start with a ride on the Isabel de Torres cable car, gliding up the mountainside for sweeping views and a stroll through lush botanical gardens. In town, visitors can explore the pastel‑colored Victorian buildings, browse local crafts, or tour the Amber Museum to learn about the region’s famous golden gemstone. For beach lovers, the coastline offers soft sand and turquoise water perfect for swimming or enjoying a Dominican lunch by the sea. Adventurers can head to the 27 Waterfalls of Damajagua for an unforgettable hike, swim, and cascade‑jumping experience. Whether you choose culture, nature, or pure relaxation, Puerto Plata delivers a warm and memorable Caribbean day.

Day 6: Monday, October 25 - Samana, Dominican Republic - 7am - 3pm

A day in Samaná offers cruise passengers a chance to experience some of the Dominican Republic’s most breathtaking natural wonders. Adventurers can ride horseback through lush rainforest to the spectacular El Limón Waterfall, a 130‑foot cascade where visitors can swim beneath the falls. Others may choose a boat trip to Cayo Levantado (Bacardi Island), famous for its powder‑soft white sand and turquoise water—perfect for sunbathing, snorkeling, or a relaxed beach day. Nature lovers can explore Los Haitises National Park, gliding through mangrove tunnels and discovering ancient Taino cave art. 

Whether you’re seeking adventure, culture, or pure Caribbean serenity, Samaná delivers a truly memorable day ashore.

Day 7 - Tuesday, October 26 - Charlotte Amalie, St. Thomas - 10 am - 6 pm.

While there are many things to do in St. Thomas, this is where BearCruise charters our own catamaran for a sailing, snorkeling at Turtle Cove, and swimming adventure. Snacks, open bar, and and gorgeous island scenery are all on the menu!

Day 8: Wednesday, October 26 - St. Johns, Antigua, 8 am - 5 pm

A day in St. John’s offers cruise passengers a vibrant mix of beaches, history, and island charm. Many visitors head to Dickenson Bay, one of Antigua’s most beautiful and easily accessible beaches, known for its soft white sand and calm turquoise water—perfect for swimming, relaxing, or enjoying a beachfront lunch. History lovers can explore Nelson’s Dockyard, a UNESCO World Heritage Site where restored Georgian buildings overlook a picturesque harbor, and then continue up to Shirley Heights Lookout for sweeping views of English Harbour and the island’s lush coastline. Back near the port, the colorful streets of Redcliffe Quay and Heritage Quay offer boutique shopping, local crafts, and cafés just steps from the ship. Whether you choose beach time, sightseeing, or a little of both, Antigua delivers a warm, easy, and unforgettable Caribbean day.

Day 9: Wednesday, October 27 - Tortola, British Virgin Islands - 8 am - 5 pm

A day in Tortola offers cruise passengers a beautiful blend of beaches, island scenery, and laid‑back Caribbean charm. Many visitors head to Cane Garden Bay, a long, curving beach with calm turquoise water, beach bars, and plenty of space to relax or swim. Adventurers can take a short ferry to Virgin Gorda to explore the world‑famous Baths, where giant granite boulders form natural pools and grottoes—one of the Caribbean’s most iconic sights. Closer to port, travelers can wander the colorful shops and cafés of Cyril B. Romney Tortola Pier Park, or visit the peaceful J.R. O’Neal Botanical Gardens for a quiet stroll among tropical flowers. For sweeping island views, a drive up to Sage Mountain National Park reveals lush rainforest trails and panoramic vistas. Whether you choose beach time, exploration, or a mix of both, Tortola delivers a relaxed and unforgettable day in the British Virgin Islands.

Day 10 - Friday, October 29 - San Juan, Puerto Rico

We disembark the Celebrity Summit.  If you are stayiing on in San Juan, it offers a vibrant blend of history, culture, and Caribbean color. Most visitors begin in Old San Juan, where blue‑cobblestone streets wind past pastel Spanish‑colonial buildings, lively plazas, and inviting cafés. Highlights include exploring the dramatic seaside fortress of Castillo San Felipe del Morro, strolling the charming shops along Calle Fortaleza, and visiting the historic San Juan Cathedral. Food lovers can savor Puerto Rican favorites like mofongo or fresh empanadas, while beach‑seekers can head to nearby Condado or Escambrón Beach for sun and turquoise water.

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Our Sailing Route

When you book with BearCruise, you get all the BearCruise Extras: nightly cocktails,  meet-ups, private shore excursions  and events!

BearCruise guys have all the fun!

Aerial,View,Of,A,Marina,In,Puerto,Plata,Dominican,Republic
Aerial,View,Of,A,Marina,In,Puerto,Plata,Dominican,Republic
Aerial,View,Of,A,Marina,In,Puerto,Plata,Dominican,Republic

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BEARCRUISE SAILORS IN TORTOLA IN FRONT OF THE CELEBRITY SUMMIT

ISLE OF PORTLAND

Pricing:

Prices include current promotions and discounts.

Prices are per person and include all taxes and fees.

Prices are subject to change without notice.  Prices shown here are quotes taken from Celebrity on March 10, 2026 and should be used as a guideline and not a guarenteed price.  Contact BearCruise for an updated quote if you are interested in booking.

Prices do not include on-board gratuities of $20 per person per day.

The first price includes cruise fare, taxes and port fees. These fares have nonrefundable deposits as noted by “NFD”.

The second price shown includes “Perks” – the classic beverage package and basic level of Wifi (perks).   If a third price is shown, that is the price with Perks with a refundable deposit as noted by “RD”.

Deposit amounts vary on Celebrity, but for most of the cabin types shown below the deposit is $450 per person.  If the rate includes a refundable deposit, it is refundable up until final payment date which is July 22, 2027.

Double Occupancy, per person –

Aqua Class Veranda (includes breakfast and dinner in the Blu Restaurant) – $1,748 per person non-refundable deposit (NRD)/ $2,172 refundable deposit (RD) with perks

Concierge Class Veranda – $1,663 pp NRD / $2083 pp RD with perks 

Balcony (Veranda) – $1,661. pp NRD / $ 2091  RD pp with perks

Ocean View – $1,231 pp  NRD/ $ 1642 pp RD with perks

Inside – $ 1089 pp  NRD/ $ 1552 pp RD with perks

Solo Occupancy, per person

Aqua Class Veranda (includes breakfast and dinner in the Blu Restaurant) – $3,022  per person non-refundable deposit (NRD) without perks / $3,494 per person NRD with perks / $4,690 refundable deposit (RD) with perks

Concierge Class Veranda – $2,770 NRD / $3,264 NRD with perks / $4,380 RD with perks 

Balcony (Veranda) – $2,791  NRD /$ 3,285 NRD with perks / $4558 RD with perks

Ocean View – $2,155  NRD/ $2,649 NRD with perks / $ 3,452 RD pp with perks

Inside – $2,029 pp  NRD/ $ 2,523 pp NRD with perks / $ 3,250 RD pp with perks

Solo cruisers who do not want to book their own solo cabin and want to find a roommate, please read our Solo Traveler Program website for information.

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A view of quaint New England beauty.
Wish you were here!!!

Martini Bar Cocktail Hour

BearCruise Catamaran in St. Thomas

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